Details of the Researcher

PHOTO

Yoshiharu Iwabuchi
Section
Graduate School of Pharmaceutical Sciences
Job title
Professor
Degree
  • 薬学博士(東北大学)

  • 薬学修士(東北大学)

Research History 8

  • 2024/04 - Present
    Tohoku University Graduate School of Pharmaceutical Sciences

  • 2002/07 - Present
    Tohoku University Graduate School of Pharmaceutical Sciences Professor

  • 2021/04 - 2024/03
    東北大学大学院薬学研究科 研究科長

  • 1997/04 - 2002/06
    Nagasaki University Faculty of Pharmaceutical Sciences Associate Professor

  • 1995/10 - 1997/03
    Biomolecular Engineering Research Institute

  • 1992/05 - 1995/06
    Protein Engineering Research Institute

  • 1991/05 - 1992/05
    The Scripps Research Institute

  • 1989/04 - 1991/03
    日本学術振興会 特別研究員

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Education 2

  • Tohoku University Graduate School, Division of Pharmaceutical Sciences

    - 1991/03

  • Tohoku University Faculty of Pharmaceutical Science 製薬化学科

    - 1986/03

Committee Memberships 5

  • 日本薬学会 顧問

    2025/04 - Present

  • 日本薬学会 会頭

    2023/04 - 2025/03

  • 日本薬学会 副会頭

    2021/04 - 2023/03

  • 有機合成化学協会 理事

    2020/03 - 2022/02

  • 日本薬学会 化学系薬学部会 部会長

    2020/04 - 2021/03

Professional Memberships 7

  • THE JAPANESE ASSOCIATION FOR MOLECULAR TARGET THERAPY OF CANCER

  • THE JAPANESE CANCER ASSOCIATION

  • International Society of Heterocyclic Chemistry

  • American Chemical Society

  • The Society of Synthetic Organic Chemistry, Japan

  • The Chemical Society of Japan

  • The Pharmaceutical Society of Japan

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Research Interests 3

  • medicinal chemistry

  • bioorganic chemistry

  • synthetic organic chemistry

Research Areas 2

  • Life sciences / Pharmaceuticals - chemistry and drug development /

  • Nanotechnology/Materials / Molecular biochemistry /

Awards 3

  1. 学術振興賞

    2012/03 日本薬学会 高活性アルコール酸化触媒AZADOの発見と展開

  2. 優秀賞

    2006/12 日本プロセス化学会 高活性アルコール酸化触媒1-methyl-AZADOの開発と展開

  3. 研究企画賞

    2000/12 有機合成化学協会 触媒的不斉Baylis-Hillman反応の展開と活用に関する研究

Papers 256

  1. Colorimetric quantification of vancomycin by highly active nitroxyl radical compounds Peer-reviewed

    Kyoko Sugiyama, Fumiya Sato, Kentaro Yoshida, Sachiko Komatsu, Tetsuya Ono, Yusuke Sasano, Yoshiharu Iwabuchi, Tsutomu Fujimura, Yoshitomo Kashiwagi, Katsuhiko Sato

    Analytical Sciences 41 (2) 179-183 2024/11/19

    DOI: 10.1007/s44211-024-00686-5  

    ISSN: 0910-6340

    eISSN: 1348-2246

  2. Strategy for C−H Functionalization of Cubanes: From Stoichiometric Reaction to Catalytic Methodology Peer-reviewed

    Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi

    European Journal of Organic Chemistry 27 (46) 2024/11/09

    DOI: 10.1002/ejoc.202401055  

    ISSN: 1434-193X

    eISSN: 1099-0690

  3. Oxoammonium salts exert antiviral effects against coronavirus via denaturation of their spike proteins Peer-reviewed

    Ryosuke Segawa, Yusuke Sasano, Yusuke Hatakawa, Yuto Fujisawa, Shuhei Akutsu, Masanobu Uchimura, Ami Ikura, Kota Matsumoto, Kazuki Sone, Tomoyuki Oe, Yoshiharu Iwabuchi, Masashi Ito, Noriyasu Hirasawa

    Scientific Reports 14 (1) 2024/10/13

    Publisher: Springer Science and Business Media LLC

    DOI: 10.1038/s41598-024-75097-7  

    eISSN: 2045-2322

  4. Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly Functionalized Saturated (Bio)isosteres of Benzene Rings Peer-reviewed

    Shota Nagasawa, Yoshiharu Iwabuchi

    Synthesis 57 (06) 1153-1170 2024/07/04

    DOI: 10.1055/a-2360-8218  

    ISSN: 0039-7881

    eISSN: 1437-210X

  5. Controlled Aerobic Oxidative Dimerization of Hydroxystilbenoids by Chromium Catalysis Peer-reviewed

    Shota Nagasawa, Yudai Itagaki, Yusuke Sasano, Yoshiharu Iwabuchi

    Organic Letters 26 (20) 4178-4182 2024/05/10

    DOI: 10.1021/acs.orglett.4c00839  

    ISSN: 1523-7060

    eISSN: 1523-7052

  6. PurA is the main target of aurodox, a type III secretion system inhibitor Peer-reviewed

    Yoshihiro Watanabe, Takeshi Haneda, Aoi Kimishima, Asaomi Kuwae, Takuya Suga, Takahiro Suzuki, Yoshiharu Iwabuchi, Masako Honsho, Sota Honma, Masato Iwatsuki, Hidehito Matsui, Hideaki Hanaki, Naoki Kanoh, Akio Abe, Yukihiro Asami, Satoshi Ōmura

    Proceedings of the National Academy of Sciences 121 (17) 2024/04/19

    Publisher: Proceedings of the National Academy of Sciences

    DOI: 10.1073/pnas.2322363121  

    ISSN: 0027-8424

    eISSN: 1091-6490

  7. Electrochemical Characterization of a Novel Organoelectrocatalyst, 7-Azabicyclo[2.2.1]heptan-7-ol (ABHOL), and Its Application to Electrochemical Sensors Peer-reviewed

    Masaki Toda, Kyoko Sugiyama, Fumiya Sato, Yusuke Sasano, Tsutomu Fujimura, Yoshiharu Iwabuchi, Katsuhiko Sato

    Chemical and Pharmaceutical Bulletin 72 (3) 249-252 2024/03/01

    Publisher: Pharmaceutical Society of Japan

    DOI: 10.1248/cpb.c23-00710  

    ISSN: 0009-2363

    eISSN: 1347-5223

  8. Design, Synthesis, and Biological Evaluation of Water-Soluble Prodrugs of C5-Curcuminoid GO-Y030 Based on Reversible Thia-Michael Reaction Peer-reviewed

    Hiroyuki Yamakoshi, Michihiro Fukuda, Hiro Ikeda, Shogo Fujiki, Aki Kohyama, Shota Nagasawa, Hanae Shinozaki, Hiroyuki Shibata, Yoshiharu Iwabuchi

    Chemical and Pharmaceutical Bulletin 72 (1) 127-134 2024/01/30

    Publisher: Pharmaceutical Society of Japan

    DOI: 10.1248/cpb.c23-00775  

    ISSN: 0009-2363

    eISSN: 1347-5223

  9. C–H Alkylation of Cubanes via Catalytic Generation of Cubyl Radicals Peer-reviewed

    Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi

    Organic Letters 26 (3) 658-663 2024/01/18

    DOI: 10.1021/acs.orglett.3c04019  

    ISSN: 1523-7060

    eISSN: 1523-7052

  10. Biological Evaluation of Isosteric Applicability of 1,3‐Substituted Cuneanes as m‐Substituted Benzenes Enabled by Selective Isomerization of 1,4‐Substituted Cubanes Peer-reviewed

    Kan Fujiwara, Shota Nagasawa, Ryusei Maeyama, Ryosuke Segawa, Noriyasu Hirasawa, Takatsugu Hirokawa, Yoshiharu Iwabuchi

    Chemistry – A European Journal 30 (11) 2024/01/11

    Publisher: Wiley

    DOI: 10.1002/chem.202303548  

    ISSN: 0947-6539

    eISSN: 1521-3765

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    Abstract We herein evaluate a biological applicability of 1,3‐substituted cuneanes as an isostere of m‐substituted benzenes based on its structural similarity. An investigation of a method to obtain 1,3‐substituted cuneanes by selective isomerization of 1,4‐substituted cubanes enables this attempt by giving a key synthetic step to obtain a cuneane analogs of pharmaceuticals having m‐substituted benzene moiety. Biological evaluation of the synthesized analogs and in silico study of the obtained result revealed a potential usage of cuneane skeleton in medicinal chemistry.

  11. Development of a fluorous trapping reagent for rapid detection of electrophilic reactive metabolites Peer-reviewed

    Yusuke Akagi, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi

    Analytical Methods 16 (24) 3810-3814 2024

    DOI: 10.1039/d4ay00577e  

    ISSN: 1759-9660

    eISSN: 1759-9679

  12. New Dihydropyridine Derivative Attenuates NF-κB Activation via Suppression of Calcium Influx in a Mouse BV-2 Microglial Cell Line Peer-reviewed

    Kota Sato, Yuto Sasaki, Michiko Ohno-Oishi, Kuniyuki Kano, Junken Aoki, Kosuke Ohsawa, Takayuki Doi, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi, Chihiro Kawano, Yoshiyuki Hirata, Toru Nakazawa

    The Tohoku Journal of Experimental Medicine 2024

    Publisher: Tohoku University Medical Press

    DOI: 10.1620/tjem.2024.j024  

    ISSN: 0040-8727

    eISSN: 1349-3329

  13. Comprehensive Structural and Electronic Properties of 2-Azaadamantane N-Oxyl Derivatives Correlated with Their Catalytic Ability Peer-reviewed

    Yoshiharu Iwabuchi

    ACS Omega 8 49067-49072 2023/12/26

    DOI: 10.1021/ACSOMEGA.3C06902  

  14. Azetidine synthesis by La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines Peer-reviewed

    Yuse Kuriyama, Yusuke Sasano, Yoshiharu Iwabuchi

    Frontiers in Chemistry 11 2023/09/19

    Publisher: Frontiers Media SA

    DOI: 10.3389/fchem.2023.1251299  

    eISSN: 2296-2646

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    Azetidine is a prevalent structural motif found in various biologically active compounds. In this research paper, we report La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines to afford azetidines. This reaction proceeded in high yields even in the presence of acid-sensitive and Lewis basic functional groups.

  15. Determination of antibiotics by amperometry using nortropine N-oxyl, a highly active nitroxyl radical Peer-reviewed

    Tetsuya Ono, Fumiya Sato, Masayuki Kumano, Sachiko Komatsu, Kyoko Sugiyama, Kazuhiro Watanabe, Kentaro Yoshida, Yusuke Sasano, Tsutomu Fujimura, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi, Katsuhiko Sato

    Analytical Sciences 39 (10) 1771-1775 2023/06/28

    Publisher: Springer Science and Business Media LLC

    DOI: 10.1007/s44211-023-00388-4  

    ISSN: 0910-6340

    eISSN: 1348-2246

  16. Asymmetric Total Synthesis of Cytotrienin A: Late‐Stage Installation of C11 Side Chain onto the Macrolactam Scaffold Peer-reviewed

    Yuki Tateishi, Ryo Sato, Shingo Komatsu, Masatsugu Noguchi, Shota Nagasawa, Yusuke Sasano, Naoki Kanoh, Yoshiharu Iwabuchi

    Angewandte Chemie International Edition 62 (29) 2023/06/12

    Publisher: Wiley

    DOI: 10.1002/anie.202303140  

    ISSN: 1433-7851

    eISSN: 1521-3773

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    Abstract Cytotrienin A, an ansamycin‐class antibiotic, exhibits potent apoptosis‐inducing activity and has attracted much attention as a lead compound for anticancer drugs. Herein, we report a new asymmetric synthetic route to cytotrienin A, employing an unexplored approach involving the late‐stage installation of a C11 side chain onto the macrolactam core. In this strategy, we utilized the redox properties of hydroquinone and installed a side chain on the sterically hindered C11 hydroxy group by the traceless Staudinger reaction. This study also demonstrated that the boron‐Wittig/iterative Suzuki–Miyaura cross‐coupling sequence was effective for the concise and selective construction of the (E,E,E)‐conjugated triene moiety. The developed route opens new opportunities for the structure–activity relationship studies of the side chains of these ansamycin antibiotics and the preparation of other synthetic analogs and chemical probes for further biological studies.

  17. That’s why I can’t stop doing research

    Yoshiharu Iwabuchi

    Journal of Synthetic Organic Chemistry, Japan 81 (6) 626-629 2023/06/01

    DOI: 10.5059/yukigoseikyokaishi.81.626  

    ISSN: 0037-9980

    eISSN: 1883-6526

  18. Mono-Carbonyl Curcumin Analogs for Cancer Therapy Peer-reviewed

    Takashi MaruYama, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi, Hiroyuki Shibata

    Biological and Pharmaceutical Bulletin 46 (6) 756-763 2023/06/01

    Publisher: Pharmaceutical Society of Japan

    DOI: 10.1248/bpb.b23-00103  

    ISSN: 0918-6158

    eISSN: 1347-5215

  19. 4‐Chloro‐2‐azaadamantane N‐Oxyl (4‐Cl‐AZADO): A Readily Preparable Organocatalyst for NOx Co‐catalyzed Aerobic Alcohol Oxidation

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    Asian Journal of Organic Chemistry 12 (4) 2023/02/17

    DOI: 10.1002/ajoc.202300031  

    ISSN: 2193-5807

    eISSN: 2193-5815

  20. Identification of the Optimal Framework for Nitroxyl Radical/Hydroxylamine in Copper-Cocatalyzed Aerobic Alcohol Oxidation Peer-reviewed

    Yoshiharu Iwabuchi

    The Journal of Organic Chemistry 88 (3) 1434-1444 2023/02/03

    DOI: 10.1021/ACS.JOC.2C02327  

    ISSN: 0022-3263 1520-6904

  21. Selective Synthesis of 1,3-Substituted Cuneanes: En Route to Potent Bioisosteres of m-Substituted Benzenes

    Yoshiharu Iwabuchi

    ChemRxiv 2023

    DOI: 10.26434/CHEMRXIV-2023-FGXXM-V2  

  22. Selective Synthesis of 1,3-Substituted Cuneanes: En Route to Potent Bioisosteres of m-Substituted Benzenes

    Yoshiharu Iwabuchi

    ChemRxiv 2023

    DOI: 10.26434/CHEMRXIV-2023-FGXXM  

  23. C-H Alkylation of Cubanes via Polar Effect-Assisted Photocatalytic Generation of Cubyl Radicals

    Yoshiharu Iwabuchi

    ChemRxiv 2023

    DOI: 10.26434/CHEMRXIV-2023-S8FKR  

  24. A Nitrile-Tagged Raman Sensor for the Ratiometric Detection of Thiols in Live Cells

    Yoshiharu Iwabuchi

    ChemRxiv 2023

    DOI: 10.26434/CHEMRXIV-2023-0LKM0  

  25. EXAMINATION OF THE EFFECTIVENESS OF DIABETIC NEPHROPATHY TREATMENT TARGETING CHREBP ACTIVITY

    Yoshiharu Iwabuchi

    Journal of Hypertension 2023

  26. Ratiometric analysis of reversible thia-Michael reactions using nitrile-tagged molecules by Raman microscopy Peer-reviewed

    Hiroyuki Yamakoshi, Daiki Shibata, Kazuki Bando, Shinji Kajimoto, Aki Kohyama, Syusuke Egoshi, Kosuke Dodo, Yoshiharu Iwabuchi, Mikiko Sodeoka, Katsumasa Fujita, Takakazu Nakabayashi

    Chemical Communications 59 (98) 14563-14566 2023

    Publisher: Royal Society of Chemistry (RSC)

    DOI: 10.1039/d3cc05015g  

    ISSN: 1359-7345

    eISSN: 1364-548X

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    Ratiometric Raman analysis of reversible thia-Michael reactions was achieved using α-cyanoacrylic acid (αCNA) derivatives.

  27. Sequential click modification of a lithium-ion endohedral fullerene connecting small molecules through a dieneazide linker Peer-reviewed

    Shogo Fujiki, Takumi Takada, Shota Nagasawa, Hiroshi Okada, Yusuke Sasano, Eunsang Kwon, Yutaka Matsuo, Yoshiharu Iwabuchi

    Chemical Communications 59 (9) 1237-1240 2023

    DOI: 10.1039/d2cc06301h  

    ISSN: 1359-7345

    eISSN: 1364-548X

  28. Electrochemical reactions of highly active nitroxyl radicals with thiol compounds Peer-reviewed

    Masayuki Kumano, Kyoko Sugiyama, Fumiya Sato, Sachiko Komatsu, Kazuhiro Watanabe, Tetsuya Ono, Kentaro Yoshida, Yusuke Sasano, Yoshiharu Iwabuchi, Tsutomu Fujimura, Yoshitomo Kashiwagi, Katsuhiko Sato

    Analytical Sciences 2022/12/28

    DOI: 10.1007/s44211-022-00246-9  

    ISSN: 0910-6340

    eISSN: 1348-2246

  29. Enantiocontrolled Access to an Intermediate for Highly Functionalized Clovane-Type Terpenoids: Formal Synthesis of Rumphellclovane E Peer-reviewed

    Daigo Ninomiya, Shota Nagasawa, Yoshiharu Iwabuchi

    Organic Letters 24 (41) 7572-7576 2022/10/11

    DOI: 10.1021/acs.orglett.2c02960  

    ISSN: 1523-7060

    eISSN: 1523-7052

  30. Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy for the Heronamide C-type Polyene Macrolactams and Their Conformational and Reactivity Analysis Peer-reviewed

    Naoki Kanoh, Yuta Terajima, Suguru Tanaka, Ryusei Terashima, Hiromichi Nishiyama, Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi, Shinichi Nishimura, Hideaki Kakeya

    The Journal of Organic Chemistry 86 (23) 16231-16248 2021/12/03

    DOI: 10.1021/acs.joc.1c01760  

    ISSN: 0022-3263

    eISSN: 1520-6904

  31. A chalcone derivative suppresses TSLP induction in mice and human keratinocytes through binding to BET family proteins Peer-reviewed

    Ryosuke Segawa, Hiroyuki Takeda, Takeshi Yokoyama, Momoha Ishida, Chihiro Miyata, Taiji Saito, Ryosuke Ishihara, Tomoya Nakagita, Yusuke Sasano, Naoki Kanoh, Yoshiharu Iwabuchi, Mineyuki Mizuguchi, Masahiro Hiratsuka, Noriyasu Hirasawa

    Biochemical Pharmacology 194 114819-114819 2021/12

    DOI: 10.1016/j.bcp.2021.114819  

    ISSN: 0006-2952

    eISSN: 1873-2968

  32. Ortho-C-H Acetoxylation of Cubane Enabling Access to Cubane Analogues of Pharmaceutically Relevant Scaffolds Peer-reviewed

    Shota Nagasawa, Masaki Hosaka, Yoshiharu Iwabuchi

    Organic Letters 23 (22) 8717-8721 2021/11/19

    DOI: 10.1021/acs.orglett.1c03144  

    ISSN: 1523-7060

    eISSN: 1523-7052

  33. Design, Synthesis, and Antifungal Activity of 16,17-Dihydroheronamide C and ent-Heronamide C Peer-reviewed

    Naoki Kanoh, Ryusei Terashima, Hiromichi Nishiyama, Yuta Terajima, Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi, Hiroaki Saito, Syusuke Egoshi, Kosuke Dodo, Mikiko Sodeoka, Chengqian Pan, Yoshinobu Ikeuchi, Shinichi Nishimura, Hideaki Kakeya

    The Journal of Organic Chemistry 86 (23) 16249-16258 2021/11/16

    DOI: 10.1021/acs.joc.1c01761  

    ISSN: 0022-3263

    eISSN: 1520-6904

  34. Nitroxyl Radical/Copper-Catalyzed Electrooxidation of Alcohols and Amines at Low Potentials Peer-reviewed

    Kyoko Sugiyama, Yusuke Sasano, Sachiko Komatsu, Kentaro Yoshida, Tetsuya Ono, Tsutomu Fujimura, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi, Katsuhiko Sato

    Chemical and Pharmaceutical Bulletin 69 (10) 1005-1009 2021/10/01

    DOI: 10.1248/cpb.c21-00409  

    ISSN: 0009-2363

    eISSN: 1347-5223

  35. The Curcumin Analog GO-Y030 Controls the Generation and Stability of Regulatory T Cells Peer-reviewed

    Takashi MaruYama, Shuhei Kobayashi, Hiroko Nakatsukasa, Yuki Moritoki, Daiki Taguchi, Yoichi Sunagawa, Tatsuya Morimoto, Atsuko Asao, Wenwen Jin, Yuji Owada, Naoto Ishii, Yoshiharu Iwabuchi, Akihiko Yoshimura, WanJun Chen, Hiroyuki Shibata

    Frontiers in Immunology 12 2021/06/23

    DOI: 10.3389/fimmu.2021.687669  

    ISSN: 1664-3224

    eISSN: 1664-3224

  36. Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols Peer-reviewed

    Shota Nagasawa, Shogo Fujiki, Yusuke Sasano, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 86 (9) 6952-6968 2021/05

    DOI: 10.1021/acs.joc.1c00438  

    ISSN: 0022-3263

    eISSN: 1520-6904

  37. Expansion of Substrate Scope for Nitroxyl Radical/Copper-Catalyzed Aerobic Oxidation of Primary Alcohols: A Guideline for Catalyst Selection Peer-reviewed

    Yusuke Sasano, Aoto Yamaichi, Ryota Sasaki, Shota Nagasawa, Yoshiharu Iwabuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN 69 (5) 488-497 2021/05

    DOI: 10.1248/cpb.c21-00043  

    ISSN: 0009-2363

    eISSN: 1347-5223

  38. Electrochemical Evaluation of Nitroxyl Radical Catalysts and Electrochemical Detection of Cyclosporin A Peer-reviewed

    Sachiko Komatsu, Yusuke Sasano, Kyoko Sugiyama, Kazuhiro Watanabe, Masayuki Kumano, Kentaro Yoshida, Tetsuya Ono, Yoshiharu Iwabuchi, Tsutomu Fujimura, Katsuhiko Sato, Yoshitomo Kashiwagi

    INTERNATIONAL JOURNAL OF ELECTROCHEMICAL SCIENCE 16 (2) 1-9 2021/02

    DOI: 10.20964/2021.02.30  

    ISSN: 1452-3981

    eISSN: 1452-3981

  39. Design, Synthesis and Biological Activity of 16,17-Dihydroheronamide C and ent-Heronamide C

    Yoshiharu Iwabuchi

    ChemRxiv 2021

    DOI: 10.26434/CHEMRXIV-2021-278L6-V2  

  40. Synthetic Access to gem-Difluoropropargyl Vinyl Ethers and Their Application to Propargyl Claisen Rearrangement Peer-reviewed

    Toshitaka Okamura, Kenta Koyamada, Junichiro Kanazawa, Kazunori Miyamoto, Yoshiharu Iwabuchi, Masanobu Uchiyama, Naoki Kanoh

    JOURNAL OF ORGANIC CHEMISTRY 86 (2) 1911-1924 2021/01

    DOI: 10.1021/acs.joc.0c01777  

    ISSN: 0022-3263

    eISSN: 1520-6904

  41. Catalysis of electro-oxidation of antibiotics by nitroxyl radicals and the electrochemical sensing of vancomycin Peer-reviewed

    Tetsuya Ono, Kyoko Sugiyama, Sachiko Komatsu, Masayuki Kumano, Kentaro Yoshida, Takenori Dairaku, Tsutomu Fujimura, Yusuke Sasano, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi, Katsuhiko Sato

    RSC Advances 11 (35) 21622-21628 2021

    DOI: 10.1039/d1ra03681e  

    eISSN: 2046-2069

  42. Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)(3) Peer-reviewed

    Yuse Kuriyama, Yusuke Sasano, Yoshihiko Hoshino, Shun-ichiro Uesugi, Aoto Yamaichi, Yoshiharu Iwabuchi

    CHEMISTRY-A EUROPEAN JOURNAL 27 (6) 1961-1965 2021/01

    DOI: 10.1002/chem.202004455  

    ISSN: 0947-6539

    eISSN: 1521-3765

  43. The Synthetic Curcumin Analogue GO-Y030 Effectively Suppresses the Development of Pressure Overload-induced Heart Failure in Mice Peer-reviewed

    Kana Shimizu, Yoichi Sunagawa, Masafumi Funamoto, Hiroki Wakabayashi, Mai Genpei, Yusuke Miyazaki, Yasufumi Katanasaka, Nurmila Sari, Satoshi Shimizu, Ayumi Katayama, Hiroyuki Shibata, Yoshiharu Iwabuchi, Hideaki Kakeya, Hiromichi Wada, Koji Hasegawa, Tatsuya Morimoto

    SCIENTIFIC REPORTS 10 (1) 2020/04

    DOI: 10.1038/s41598-020-64207-w  

    ISSN: 2045-2322

  44. Electrochemical determination of choline using nortropine-N-oxyl for a non-enzymatic system Peer-reviewed

    Yoshitomo Kashiwagi, Tetsuya Ono, Fumiya Sato, Masayuki Kumano, Kentaro Yoshida, Takenori Dairaku, Yusuke Sasano, Yoshiharu Iwabuchi, Katsuhiko Sato

    SENSING AND BIO-SENSING RESEARCH 27 2020/02

    DOI: 10.1016/j.sbsr.2019.100302  

    eISSN: 2214-1804

  45. Highly Chemoselective gem-Difluoropropargylation of Aliphatic Alcohols Peer-reviewed

    Toshitaka Okamura, Syusuke Egoshi, Kosuke Dodo, Mikiko Sodeoka, Yoshiharu Iwabuchi, Naoki Kanoh

    CHEMISTRY-A EUROPEAN JOURNAL 25 (70) 16002-16006 2019/12

    DOI: 10.1002/chem.201904366  

    ISSN: 0947-6539

    eISSN: 1521-3765

  46. An integrated screening system for the selection of exemplary substrates for natural and engineered cytochrome P450s Peer-reviewed

    Naoki Kanoh, Ayano Kawamata-Asano, Kana Suzuki, Yusuke Takahashi, Takeshi Miyazawa, Takemichi Nakamura, Takashi Moriya, Hiroyuki Hirano, Hiroyuki Osada, Yoshiharu Iwabuchi, Shunji Takahashi

    SCIENTIFIC REPORTS 9 (1) 18023 2019/12

    DOI: 10.1038/s41598-019-54473-8  

    ISSN: 2045-2322

  47. Methyl-Selective alpha-Oxygenation of Tertiary Amines to Formamides by Employing Copper/Moderately Hindered Nitroxyl Radical (DMN-AZADO or 1-Me-AZADO) Peer-reviewed

    Satoru Nakai, Takafumi Yatabe, Kosuke Suzuki, Yusuke Sasano, Yoshiharu Iwabuchi, Junya Hasegawa, Noritaka Mizuno, Kazuya Yamaguchi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58 (46) 16651-16659 2019/11

    DOI: 10.1002/anie.201909005  

    ISSN: 1433-7851

    eISSN: 1521-3773

  48. Gold(I)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex Peer-reviewed

    Toshitaka Okamura, Shogo Fujiki, Yoshiharu Iwabuchi, Naoki Kanoh

    ORGANIC & BIOMOLECULAR CHEMISTRY 17 (37) 8522-8526 2019/10

    DOI: 10.1039/c9ob01348b  

    ISSN: 1477-0520

    eISSN: 1477-0539

  49. クルクミンをリード化合物としたヒストンアセチル化酵素活性を指標とする新規心不全治療薬の探索

    清水 果奈, 船本 雅文, 砂川 陽一, 刀坂 泰史, 宮崎 雄輔, Sari Nurmila, 清水 聡史, 柴田 浩行, 岩渕 好治, 和田 啓道, 長谷川 浩二, 森本 達也

    日本抗加齢医学会総会プログラム・抄録集 19回 234-234 2019/06

    Publisher: (一社)日本抗加齢医学会

  50. Recent Progress in Oxidative Organic Transformations Employing Nitroxyl Radicals Peer-reviewed

    Yoshiharu Iwabuchi

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 77 (5) 424-432 2019/05

    DOI: 10.5059/yukigoseikyokaishi.77.424  

    ISSN: 0037-9980

  51. Ln(OTf)(3)-catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols Peer-reviewed

    Daichi Nakamura, Yusuke Sasano, Yoshiharu Iwabuchi

    ORGANIC & BIOMOLECULAR CHEMISTRY 17 (14) 3581-3589 2019/04

    DOI: 10.1039/c8ob02448k  

    ISSN: 1477-0520

    eISSN: 1477-0539

  52. Electrochemical Detection of Triglycerides Based on an Enzymatic Reaction and Electrocatalytic Oxidation with Nortropine-N-oxyl

    Tetsuya Ono, Katsuhiko Sato, Yusuke Sasano, Kentaro Yoshida, Takenori Dairaku, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi

    ELECTROANALYSIS 31 (4) 603-606 2019/04

    DOI: 10.1002/elan.201800660  

    ISSN: 1040-0397

    eISSN: 1521-4109

  53. Safe and Scalable Aerobic Oxidation by 2-Azaadamantan-2-ol (AZADOL)/NOx Catalysis: Large-Scale Preparation of Shi's Catalyst

    Yusuke Sasano, Hikaru Sato, Shinsuke Tadokoro, Masami Kozawa, Yoshiharu Iwabuchi

    ORGANIC PROCESS RESEARCH & DEVELOPMENT 23 (4) 571-577 2019/04

    DOI: 10.1021/acs.oprd.8b00456  

    ISSN: 1083-6160

    eISSN: 1520-586X

  54. Green Oxidative Synthesis of Aldehydes and Ketones

    Yoshiharu Iwabuchi

    Green Oxidation in Organic Synthesis 2019

  55. Electrochemical Oxidation of Amines Using a Nitroxyl Radical Catalyst and the Electroanalysis of Lidocaine Peer-reviewed

    Katsuhiko Sato, Tetsuya Ono, Yusuke Sasano, Fumiya Sato, Masayuki Kumano, Kentaro Yoshida, Takenori Dairaku, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi

    Catalysts 8 (12) 649-649 2018/12

    DOI: 10.3390/catal8120649  

    ISSN: 2073-4344

    eISSN: 2073-4344

  56. Dietary intake of pyrolyzed deketene curcumin inhibits gastric carcinogenesis Peer-reviewed

    Taichi Yoshida, Takashi Maruyama, Masatomo Miura, Masahiro Inoue, Koji Fukuda, Kazuhiro Shimazu, Daiki Taguchi, Hiroaki Kanda, Masanobu Oshima, Yoshiharu Iwabuchi, Hiroyuki Shibata

    JOURNAL OF FUNCTIONAL FOODS 50 192-200 2018/11

    DOI: 10.1016/j.jff.2018.09.033  

    ISSN: 1756-4646

  57. 2-Azaadamantane N-oxyl (AZADO)/Cu Catalysis Enables Chemoselective Aerobic Oxidation of Alcohols Containing Electron-Rich Divalent Sulfur Functionalities Peer-reviewed

    Yusuke Sasano, Naoki Kogure, Shota Nagasawa, Koki Kasabata, Yoshiharu Iwabuchi

    ORGANIC LETTERS 20 (19) 6104-6107 2018/10

    DOI: 10.1021/acs.orglett.8b02528  

    ISSN: 1523-7060

    eISSN: 1523-7052

  58. Curcumin analog, GO-Y078, overcomes resistance to tumor angiogenesis inhibitors Peer-reviewed

    Kazuhiro Shimazu, Masahiro Inoue, Shunsuke Sugiyama, Koji Fukuda, Taichi Yoshida, Daiki Taguchi, Yoshihiko Uehara, Sei Kuriyama, Masamitsu Tanaka, Masatomo Miura, Hiroshi Nanjyo, Yoshiharu Iwabuchi, Hiroyuki Shibata

    CANCER SCIENCE 109 (10) 3285-3293 2018/08/16

    DOI: 10.1111/cas.13741   10.1248/bpb.b23-00103_references_DOI_U3hHv60R4aT4ximOkZqIwU2fmRV  

    ISSN: 1347-9032

    eISSN: 1349-7006

  59. CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides Peer-reviewed

    Kengo Kataoka, Keiju Wachi, Xiongjie Jin, Kosuke Suzuki, Yusuke Sasano, Yoshiharu Iwabuchi, Jun-ya Hasegawa, Noritaka Mizuno, Kazuya Yamaguchi

    CHEMICAL SCIENCE 9 (21) 4756-4768 2018/06

    DOI: 10.1039/c8sc01410h  

    ISSN: 2041-6520

    eISSN: 2041-6539

  60. Expedient Entry to 1-Aminoadamantane Derivatives via Aza-Prins Cyclization of 7-Methylenebicyclo[3.3.1]nonan-3-one Oximes Peer-reviewed

    Tetsuya Kuga, Yusuke Sasano, Masaki Tomizawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

    SYNTHESIS-STUTTGART 50 (9) 1820-1826 2018/05

    DOI: 10.1055/s-0036-1591920  

    ISSN: 0039-7881

    eISSN: 1437-210X

  61. Stereocontrolled Construction of ABCD Tetracyclic Ring System with Vicinal All-Carbon Quaternary Stereogenic Centers of Calyciphylline A Type Alkaloids Peer-reviewed

    Yusuke Sasano, Junpei Koyama, Kaori Yoshikawa, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

    ORGANIC LETTERS 20 (10) 3053-3056 2018/05

    DOI: 10.1021/acs.orglett.8b01087  

    ISSN: 1523-7060

    eISSN: 1523-7052

  62. IBX as a catalyst for dehydration of hydroperoxides: green entry to alpha,beta-unsaturated ketones via oxygenative allylic transposition Peer-reviewed

    Tetsuya Kuga, Yusuke Sasano, Yoshiharu Iwabuchi

    CHEMICAL COMMUNICATIONS 54 (7) 798-801 2018/01

    DOI: 10.1039/c7cc08957k  

    ISSN: 1359-7345

    eISSN: 1364-548X

  63. Synthetic Analogs of Curcumin as Modulators of Multidrug Resistance-Linked ABC Transporters Peer-reviewed

    Megumi Murakami, Shinobu Ohnuma, Katsuyoshi Kudoh, Masaharu Ishida, Yoshiharu Iwabuchi, Hiroyuki Shibata, Hiroki Hayashi, Fuyuhiko Motoi, Takeshi Naitoh, Michiaki Unno

    CANCER SCIENCE 109 63-63 2018/01

    ISSN: 1349-7006

  64. Synthetic Analogs of Curcumin Modulate the Function of Multidrug Resistance-Linked ATP-Binding Cassette Transporter ABCG2 Peer-reviewed

    Megumi Murakami, Shinobu Ohnuma, Michihiro Fukuda, Eduardo E. Chufan, Katsuyoshi Kudoh, Keigo Kanehara, Norihiko Sugisawa, Masaharu Ishida, Takeshi Naitoh, Hiroyuki Shibata, Yoshiharu Iwabuchi, Suresh V. Ambudkar, Michiaki Unno

    DRUG METABOLISM AND DISPOSITION 45 (11) 1166-1177 2017/11

    DOI: 10.1124/dmd.117.076000  

    ISSN: 0090-9556

    eISSN: 1521-009X

  65. Substrate Recognition by a Dual-Function P450 Monooxygenase GfsF Involved in FD-891 Biosynthesis Peer-reviewed

    Akimasa Miyanaga, Ryuichi Takayanagi, Takashi Furuya, Ayano Kawamata, Tomohiro Itagaki, Yoshiharu Iwabuchi, Naoki Kanoh, Fumitaka Kudo, Tadashi Eguchi

    CHEMBIOCHEM 18 (21) 2179-2187 2017/11

    DOI: 10.1002/cbic.201700429  

    ISSN: 1439-4227

    eISSN: 1439-7633

  66. Nazarov Cyclization Entry to Chiral Bicyclo[5.3.0]decanoid Building Blocks and Its Application to Formal Synthesis of (-)-Englerin A Peer-reviewed

    Keisuke Morisaki, Yusuke Sasano, Takahiro Koseki, Takuro Shibuta, Naoki Kanoh, Wen-Hua Chiou, Yoshiharu Iwabuchi

    ORGANIC LETTERS 19 (19) 5142-5145 2017/10

    DOI: 10.1021/acs.orglett.7b02428  

    ISSN: 1523-7060

    eISSN: 1523-7052

  67. A mild two-step propargylation of aromatic bioactive small molecules

    Naoki Kanoh, Toshitaka Okamura, Takahiro Suzuki, Yoshiharu Iwabuchi

    ORGANIC & BIOMOLECULAR CHEMISTRY 15 (34) 7190-7195 2017/09

    DOI: 10.1039/c7ob01587a  

    ISSN: 1477-0520

    eISSN: 1477-0539

  68. Catalytic Oxygenative Allylic Transposition of Alkenes into Enones with an Azaadamantane-Type Oxoammonium Salt Catalyst

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    CHEMISTRY-A EUROPEAN JOURNAL 23 (43) 10276-10279 2017/08

    DOI: 10.1002/chem.201702512  

    ISSN: 0947-6539

    eISSN: 1521-3765

  69. Synthetic analogs of curcumin as modulators of multidrug resistance-linked ABC transporters Peer-reviewed

    Megumi Obara, Shinobu Ohnuma, Eduardo E. Chufan, Masaharu Ishida, Katsuyoshi Kudoh, Norihiko Sugisawa, Hideo Ohtsuka, Takeshi Naitoh, Hiroyuki Shibata, Yoshiharu Iwabuchi, Suresh V. Ambudkar, Michiaki Unno

    CANCER RESEARCH 77 2017/07

    DOI: 10.1158/1538-7445.AM2017-3242  

    ISSN: 0008-5472

    eISSN: 1538-7445

  70. Concise, Protecting-Group-Free Synthesis of (+)-Nemonapride via Eu(OTf)(3)-Catalyzed Aminolysis of 3,4-Epoxy Alcohol Peer-reviewed

    Shun-ichiro Uesugi, Yusuke Sasano, Shogo Matsui, Naoki Kanoh, Yoshiharu Iwabuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN 65 (1) 22-24 2017/01

    DOI: 10.1248/cpb.c16-00568  

    ISSN: 0009-2363

  71. Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts Peer-reviewed

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    SYNLETT 28 (1) A13-A16 2017/01

    ISSN: 0936-5214

    eISSN: 1437-2096

  72. Design and synthesis of the penta(acetoxymethyl) ester of dioctanoyl phosphatidylinositol-3,5-bisphosphate Peer-reviewed

    Naoki Kanoh, Kosuke Mano, Daisuke Saigusa, Takeo Usui, Yoshiharu Iwabuchi

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 26 (23) 5770-5772 2016/12

    DOI: 10.1016/j.bmcl.2016.10.046  

    ISSN: 0960-894X

    eISSN: 1464-3405

  73. Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts Peer-reviewed

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 55 (42) 13189-13194 2016/10

    DOI: 10.1002/anie.201607752  

    ISSN: 1433-7851

    eISSN: 1521-3773

  74. Asymmetric Total Synthesis of Heronamides A-C: Stereochemical Confirmation and Impact of Long-Range Stereochemical Communication on the Biological Activity Peer-reviewed

    Naoki Kanoh, Shunya Itoh, Kohei Fujita, Kohei Sakanishi, Ryosuke Sugiyama, Yuta Terajima, Yoshiharu Iwabuchi, Shinichi Nishimura, Hideaki Kakeya

    CHEMISTRY-A EUROPEAN JOURNAL 22 (25) 8586-8595 2016/06

    DOI: 10.1002/chem.201600569  

    ISSN: 0947-6539

    eISSN: 1521-3765

  75. Identification of anti-cancer chemical compounds using Xenopus embryos Peer-reviewed

    Masamitsu Tanaka, Sei Kuriyama, Go Itoh, Aki Kohyama, Yoshiharu Iwabuchi, Hiroyuki Shibata, Masakazu Yashiro, Namiko Aiba

    CANCER SCIENCE 107 (6) 803-811 2016/06

    DOI: 10.1111/cas.12940  

    ISSN: 1347-9032

    eISSN: 1349-7006

  76. Vicenistatin induces early endosome-derived vacuole formation in mammalian cells Peer-reviewed

    Yuko Nishiyama, Tomohiro Ohmichi, Sayaka Kazami, Hiroki Iwasaki, Kousuke Mano, Yoko Nagumo, Fumitaka Kudo, Sosaku Ichikawa, Yoshiharu Iwabuchi, Naoki Kanoh, Tadashi Eguchi, Hiroyuki Osada, Takeo Usui

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 80 (5) 902-910 2016/05

    DOI: 10.1080/09168451.2015.1132152  

    ISSN: 0916-8451

    eISSN: 1347-6947

  77. Synthesis and structure-activity relationship study of FD-891: importance of the side chain and C8-C9 epoxide for cytotoxic activity against cancer cells Peer-reviewed

    Tomohiro Itagaki, Ayano Kawamata, Miho Takeuchi, Keisuke Hamada, Yoshiharu Iwabuchi, Tadashi Eguchi, Fumitaka Kudo, Takeo Usui, Naoki Kanoh

    JOURNAL OF ANTIBIOTICS 69 (4) 287-293 2016/04

    DOI: 10.1038/ja.2015.148  

    ISSN: 0021-8820

  78. がん細胞遊走阻害活性天然物fusarisetin Aの合成研究

    高山 亜紀, 叶 直樹, 岩渕 好治

    日本薬学会年会要旨集 136年会 (2) 83-83 2016/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  79. An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A Peer-reviewed

    Aki Kohyama, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

    TETRAHEDRON LETTERS 57 (5) 517-519 2016/02

    DOI: 10.1016/j.tetlet.2015.12.049  

    ISSN: 0040-4039

  80. Total Synthesis of the Proposed Structure of Turkiyenine Peer-reviewed

    Hisataka Kobayashi, Yusuke Sasano, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2016 (2) 270-273 2016/01

    DOI: 10.1002/ejoc.201501365  

    ISSN: 1434-193X

    eISSN: 1099-0690

  81. A Curcumin Analog, GO-Y078, Effectively Inhibits Angiogenesis through Actin Disorganization Peer-reviewed

    Shunsuke Sugiyama, Yuki Yoshino, Sei Kuriyama, Masahiro Inoue, Keigo Komine, Kazunori Otsuka, Aki Kohyama, Hiroyuki Yamakoshi, Chikashi Ishioka, Masamitsu Tanaka, Yoshiharu Iwabuchi, Hiroyuki Shibata

    ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY 16 (5) 633-647 2016

    DOI: 10.2174/1871520615666151013125559  

    ISSN: 1871-5206

    eISSN: 1875-5992

  82. A diarylpentanoid curcumin analog exhibits improved radioprotective potential in the intestinal mucosa Peer-reviewed

    Koji Fukuda, Yoshihiko Uehara, Eiko Nakata, Masahiro Inoue, Kazuhiro Shimazu, Taichi Yoshida, Hiroaki Kanda, Hiroshi Nanjo, Yoshio Hosoi, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi, Hiroyuki Shibata

    INTERNATIONAL JOURNAL OF RADIATION BIOLOGY 92 (7) 388-394 2016

    DOI: 10.3109/09553002.2016.1164910  

    ISSN: 0955-3002

    eISSN: 1362-3095

  83. Reversibility of the thia-Michael reaction of cytotoxic C-5-curcuminoid and structure-activity relationship of bis-thiol-adducts thereof Peer-reviewed

    Aki Kohyama, Michihiro Fukuda, Shunsuke Sugiyama, Hiroyuki Yamakoshi, Naoki Kanoh, Chikashi Ishioka, Hiroyuki Shibatac, Yoshiharu Iwabuchi

    ORGANIC & BIOMOLECULAR CHEMISTRY 14 (45) 10683-10687 2016

    DOI: 10.1039/c6ob01771a  

    ISSN: 1477-0520

    eISSN: 1477-0539

  84. Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B Peer-reviewed

    Shun-ichiro Uesugi, Tsubasa Watanabe, Takamichi Imaizumi, Yu Ota, Keisuke Yoshida, Haruna Ebisu, Takumi Chinen, Yoko Nagumo, Masatoshi Shibuya, Naoki Kanoh, Takeo Usui, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 80 (24) 12333-12350 2015/12

    DOI: 10.1021/acs.joc.5b02256  

    ISSN: 0022-3263

    eISSN: 1520-6904

  85. Inhibition of beta-catenin and STAT3 with a curcumin analog suppresses gastric carcinogenesis in vivo Peer-reviewed

    Yoshihiko Uehara, Masahiro Inoue, Koji Fukuda, Hiroyuki Yamakoshi, Yoshio Hosoi, Hiroaki Kanda, Masanobu Oshima, Yoshiharu Iwabuchi, Hiroyuki Shibata

    GASTRIC CANCER 18 (4) 774-783 2015/10

    DOI: 10.1007/s10120-014-0434-3  

    ISSN: 1436-3291

    eISSN: 1436-3305

  86. Structure-Activity Relationships of the Antitumor C-5-Curcuminoid GO-Y030 Peer-reviewed

    Aki Kohyama, Hiroyuki Yamakoshi, Shoko Hongo, Naoki Kanoh, Hiroyuki Shibata, Yoshiharu Iwabuchi

    MOLECULES 20 (8) 15374-15391 2015/08

    DOI: 10.3390/molecules200815374  

    ISSN: 1420-3049

  87. Irciniastatin A Induces Potent and Sustained Activation of Extracellular Signal-Regulated Kinase and Thereby Promotes Ectodomain Shedding of Tumor Necrosis Factor Receptor 1 in Human Lung Carcinoma A549 Cells Peer-reviewed

    Hue Tu Quach, Seiya Hirano, Sayuri Fukuhara, Tsubasa Watanabe, Naoki Kanoh, Yoshiharu Iwabuchi, Takeo Usui, Takao Kataoka

    BIOLOGICAL & PHARMACEUTICAL BULLETIN 38 (6) 941-946 2015/06

    DOI: 10.1248/bpb.b15-00078  

    ISSN: 0918-6158

  88. Irciniastatin A, a pederin-type translation inhibitor, promotes ectodomain shedding of cell-surface tumor necrosis factor receptor 1 Peer-reviewed

    Seiya Hirano, Hue Tu Quach, Tsubasa Watanabe, Naoki Kanoh, Yoshiharu Iwabuchi, Takeo Usui, Takao Kataoka

    JOURNAL OF ANTIBIOTICS 68 (6) 417-420 2015/06

    DOI: 10.1038/ja.2015.3  

    ISSN: 0021-8820

  89. Highly Efficient Aerobic Oxidation of Alcohols by Using Less-Hindered Nitroxyl-Radical/Copper Catalysis: Optimum Catalyst Combinations and Their Substrate Scope Peer-reviewed

    Yusuke Sasano, Naoki Kogure, Tomohiro Nishiyama, Shota Nagasawa, Yoshiharu Iwabuchi

    CHEMISTRY-AN ASIAN JOURNAL 10 (4) 1004-1009 2015/04

    DOI: 10.1002/asia.201403245  

    ISSN: 1861-4728

    eISSN: 1861-471X

  90. Third Generation Photo-Cross-Linked Small-Molecule Affinity Matrix: A Photoactivatable and Photocleavable System Enabling Quantitative Analysis of the Photo-Cross-Linked Small Molecules and Their Target Purification Peer-reviewed

    Takahiro Suzuki, Toshitaka Okamura, Takenori Tomohiro, Yoshiharu Iwabuchi, Naoki Kanoh

    BIOCONJUGATE CHEMISTRY 26 (3) 389-395 2015/03

    DOI: 10.1021/bc500559e  

    ISSN: 1043-1802

  91. Development of an Azanoradamantane-Type Nitroxyl Radical Catalyst for Class-Selective Oxidation of Alcohols Peer-reviewed

    Ryusuke Doi, Masatoshi Shibuya, Tsukasa Murayama, Yoshihiko Yamamoto, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 80 (1) 401-413 2015/01

    DOI: 10.1021/jo502426p  

    ISSN: 0022-3263

  92. Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chiral Alkoxyamines as Precatalysts: Catalyst Structure, Active Species, and Substrate Scope Peer-reviewed

    Keiichi Murakami, Yusuke Sasano, Masaki Tomizawa, Masatoshi Shibuya, Eunsang Kwon, Yoshiharu Iwabuchi

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 136 (50) 17591-17600 2014/12

    DOI: 10.1021/ja509766f  

    ISSN: 0002-7863

  93. ChemInform Abstract: Total Synthesis of the Proposed Structure of Heronamide C.

    Kohei Sakanishi, Shunya Itoh, Ryosuke Sugiyama, Shinichi Nishimura, Hideaki Kakeya, Yoshiharu Iwabuchi, Naoki Kanoh

    ChemInform 45 (49) no-no 2014/11

    Publisher: Wiley

    DOI: 10.1002/chin.201449210  

    ISSN: 0931-7597

  94. Mechanistic Insight into Aerobic Alchol Oxidation Using NOx-Nitroxide Catalysis Based on Catalyst Structure-Activity Relationships Peer-reviewed

    Masatoshi Shibuya, Shota Nagasawa, Yuji Osada, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 79 (21) 10256-10268 2014/11

    DOI: 10.1021/jo501862k  

    ISSN: 0022-3263

    eISSN: 1520-6904

  95. A Concise and Unified Strategy for Synthesis of the C1-C18 Macrolactone Fragments of FD-891, FD-892 and Their Analogues: Formal Total Synthesis of FD-891 Peer-reviewed

    Naoki Kanoh, Ayano Kawamata, Tomohiro Itagaki, Yuta Miyazaki, Kenzo Yahata, Eunsang Kwon, Yoshiharu Iwabuchi

    ORGANIC LETTERS 16 (19) 5216-5219 2014/10

    DOI: 10.1021/ol502633j  

    ISSN: 1523-7060

    eISSN: 1523-7052

  96. Strong inhibitory effects of curcumin and its demethoxy analog on Escherichia coli ATP synthase F-1 sector

    Mizuki Sekiya, Eiko Chiba, Momoe Satoh, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi, Masamitsu Futai, Mayumi Nakanishi-Matsui

    INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES 70 241-245 2014/09

    DOI: 10.1016/j.ijbiomac.2014.06.055  

    ISSN: 0141-8130

    eISSN: 1879-0003

  97. Eu(OTf)(3)-Catalyzed Highly Regioselective Nucleophilic Ring Opening of 2,3-Epoxy Alcohols: An Efficient Entry to 3-Substituted 1,2-Diol Derivatives

    Shun-ichiro Uesugi, Tsubasa Watanabe, Takamichi Imaizumi, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

    ORGANIC LETTERS 16 (17) 4408-4411 2014/09

    DOI: 10.1021/ol502264y  

    ISSN: 1523-7060

    eISSN: 1523-7052

  98. Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chirally Modified AZADOs (vol 11, pg 1829, 2009) Peer-reviewed

    Masaki Tomizawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

    ORGANIC LETTERS 16 (18) 4968-4968 2014/09

    DOI: 10.1021/ol502543r  

    ISSN: 1523-7060

    eISSN: 1523-7052

  99. NAD(P)+選択的検出プローブを利用したチトクロムP450基質スクリーニング法の構築と評価

    守谷 崇, 川又 綾乃, 高橋 裕介, 岩渕 好治, 叶 直樹

    日本薬学会年会要旨集 134年会 (2) 70-70 2014/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  100. 抗腫瘍性マクロライドFD-891およびFD-892の系統的合成研究 マクロラクトン部の構築

    板垣 友宏, 川又 綾乃, 宮崎 雄太, 八幡 健三, 叶 直樹, 岩渕 好治

    日本薬学会年会要旨集 134年会 (2) 137-137 2014/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  101. ENANTIOSELECTIVE INTRAMOLECULAR AZA-SPIROANNULATION ONTO BENZOFURANS USING CHIRAL RHODIUM CATALYSIS

    Takuro Shibuta, Shigeki Sato, Masatoshi Shibuya, Naoki Kanoh, Tohru Taniguchi, Kenji Monde, Yoshiharu Iwabuchi

    HETEROCYCLES 89 (3) 631-639 2014/03

    DOI: 10.3987/COM-14-12941  

    ISSN: 0385-5414

    eISSN: 1881-0942

  102. Total Synthesis of the Proposed Structure of Heronamide C

    Kohei Sakanishi, Shunya Itoh, Ryosuke Sugiyama, Shinichi Nishimura, Hideaki Kakeya, Yoshiharu Iwabuchi, Naoki Kanoh

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2014 (7) 1376-1380 2014/03

    DOI: 10.1002/ejoc.201301487  

    ISSN: 1434-193X

    eISSN: 1099-0690

  103. Highly Chemoselective Aerobic Oxidation of Amino Alcohols into Amino Carbonyl Compounds

    Yusuke Sasano, Shota Nagasawa, Mai Yamazaki, Masatoshi Shibuya, Jaiwook Park, Yoshiharu Iwabuchi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53 (12) 3236-3240 2014/03

    DOI: 10.1002/anie.201309634  

    ISSN: 1433-7851

    eISSN: 1521-3773

  104. Discovery and Exploitation of AZADO: The Highly Active Catalyst for Alcohol Oxidation

    Yoshiharu Iwabuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN 61 (12) 1197-1213 2013/12

    DOI: 10.1248/cpb.c13-00456  

    ISSN: 0009-2363

  105. On the Origin of cine-Substitution in the Stille Coupling of Trisubstituted Iodoalkene and trans-Vinylstannane

    Naoki Kanoh, Yutaro Ohno, Tomohiro Itagaki, Hayato Fukuda, Yoshiharu Iwabuchi

    SYNLETT 24 (20) 2660-2664 2013/12

    DOI: 10.1055/s-0033-1339899  

    ISSN: 0936-5214

    eISSN: 1437-2096

  106. 3-Methyl-4-oxa-5-azahomoadamantane: Alkoxyamine-Type Organocatalyst for Alcohol Oxidation

    Yusuke Sasano, Keiichi Murakami, Tomohiro Nishiyama, Eunsang Kwon, Yoshiharu Iwabuchi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 52 (48) 12624-12627 2013/11

    DOI: 10.1002/anie.201307144  

    ISSN: 1433-7851

    eISSN: 1521-3773

  107. C-H MODIFICATION OF 2-AZAADAMANTANE: SYNTHESIS OF C5-FUNCTIONALIZED AZADOS FOR ADVANCED USE

    Yusuke Sasano, Tomohiro Nishiyama, Masaki Tomizawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

    HETEROCYCLES 87 (10) 2109-2118 2013/10

    DOI: 10.3987/COM-13-12804  

    ISSN: 0385-5414

    eISSN: 1881-0942

  108. Development of Simple and Highly Efficient Aerobic Oxidation Method by Tuning Electrochemical and Steric Properties of Nitroxyl Radical Catalysts Peer-reviewed

    Masatoshi Shibuya, Yoshiharu Iwabuchi

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 71 (5) 515-525 2013/05

    DOI: 10.5059/yukigoseikyokaishi.71.515  

    ISSN: 0037-9980

  109. Concise Entry to Chiral 5-(4-Hydroxybutyl)-2(5H)-furanone via HTIB-Mediated Novel Oxidative Fragmentation: Formal Total Synthesis of (+)-Dubiusamine A Peer-reviewed

    Muneo Kawasumi, Yoshiharu Iwabuchi

    ORGANIC LETTERS 15 (7) 1788-1790 2013/04

    DOI: 10.1021/ol4005239  

    ISSN: 1523-7060

  110. 抗腫瘍性マクロライドFD-891およびFD-892の系統的合成研究

    川又 綾乃, 宮崎 雄太, 八幡 健三, 叶 直樹, 岩渕 好治

    日本薬学会年会要旨集 133年会 (2) 80-80 2013/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  111. 新規PI(3,5)P2誘導体の合成とvicenistatinの作用機構解析への応用

    真野 昂裕, 岩渕 好治, 臼井 健郎, 叶 直樹

    日本薬学会年会要旨集 133年会 (2) 91-91 2013/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  112. An improved fluorogenic NAD(P)(+) detection method using 2-acetylbenzofuran: its origin and application

    Takashi Moriya, Ayano Kawamata, Yusuke Takahashi, Yoshiharu Iwabuchi, Naoki Kanoh

    CHEMICAL COMMUNICATIONS 49 (98) 11500-11502 2013

    DOI: 10.1039/c3cc47264g  

    ISSN: 1359-7345

    eISSN: 1364-548X

  113. Dual Structure-Activity Relationship of Osteoclastogenesis Inhibitor Methyl Gerfelin Based on TEG Scanning Peer-reviewed

    Naoki Kanoh, Takahiro Suzuki, Makoto Kawatani, Yasuhiro Katou, Hiroyuki Osada, Yoshiharu Iwabuchi

    BIOCONJUGATE CHEMISTRY 24 (1) 44-52 2013/01

    DOI: 10.1021/bc3003666  

    ISSN: 1043-1802

  114. Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside Peer-reviewed

    Hayato Fukuda, Yuko Nishiyama, Shiina Nakamura, Yutaro Ohno, Tadashi Eguchi, Yoshiharu Iwabuchi, Takeo Usui, Naoki Kanoh

    CHEMISTRY-AN ASIAN JOURNAL 7 (12) 2872-2881 2012/12

    DOI: 10.1002/asia.201200615  

    ISSN: 1861-4728

  115. Nitroxyl Radical/Phl(OAc)(2): One-Pot Oxidative Cleavage of Vicinal Diols to (Di)Carboxylic Acids Peer-reviewed

    Masatoshi Shibuya, Takuro Shibuta, Hayato Fukuda, Yoshiharu Iwabuchi

    ORGANIC LETTERS 14 (19) 5010-5013 2012/10

    DOI: 10.1021/ol3021435  

    ISSN: 1523-7060

    eISSN: 1523-7052

  116. Organocatalytic One-Pot Oxidative Cleavage of Terminal Diols to Dehomologated Carboxylic Acids Peer-reviewed

    Masatoshi Shibuya, Ryusuke Doi, Takuro Shibuta, Shun-ichiro Uesugi, Yoshiharu Iwabuchi

    ORGANIC LETTERS 14 (19) 5006-5009 2012/10

    DOI: 10.1021/ol3021429  

    ISSN: 1523-7060

    eISSN: 1523-7052

  117. Oxidation of nitroxyl radicals: electrochemical and computational studies Peer-reviewed

    Masatoshi Shibuya, Fabio Pichierri, Masaki Tomizawa, Shota Nagasawa, Iwao Suzuki, Yoshiharu Iwabuchi

    TETRAHEDRON LETTERS 53 (16) 2070-2073 2012/04

    DOI: 10.1016/j.tetlet.2012.02.033  

    ISSN: 0040-4039

  118. Catalytic Oxidation of Silyl Enol Ethers to 1,2-Diketones Employing Nitroxyl Radicals Peer-reviewed

    Masaki Hayashi, Masatoshi Shibuya, Yoshiharu Iwabuchi

    SYNLETT (7) 1025-1030 2012/04

    DOI: 10.1055/s-0031-1290528  

    ISSN: 0936-5214

    eISSN: 1437-2096

  119. Oxidation of Alcohols to Carbonyl Compounds with Diisopropyl Azodicarboxylate Catalyzed by Nitroxyl Radicals Peer-reviewed

    Masaki Hayashi, Masatoshi Shibuya, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 77 (6) 3005-3009 2012/03

    DOI: 10.1021/jo300088b  

    ISSN: 0022-3263

    eISSN: 1520-6904

  120. Challenges in establishing potent cancer chemotherapy using newly synthesized 1,5-Diaryl-3-Oxo-1,4-Pentadiene analogs of curcumin

    Hiroyuki Shibata, Yoshiharu Iwabuchi

    Curcumin: Biosynthesis, Medicinal Uses and Health Benefits 177-191 2012/02/01

  121. Oxidative Conversion of Silyl Enol Ethers to alpha,beta-Unsaturated Ketones Employing Oxoammonium Salts Peer-reviewed

    Masaki Hayashi, Masatoshi Shibuya, Yoshiharu Iwabuchi

    ORGANIC LETTERS 14 (1) 154-157 2012/01

    DOI: 10.1021/ol2029417  

    ISSN: 1523-7060

    eISSN: 1523-7052

  122. Detection of Cytochrome P450 Substrates by Using a Small-Molecule Droplet Array on an NADH-Immobilized Solid Surface

    Hiroshi Takayama, Shunji Takahashi, Takashi Moriya, Hiroyuki Osada, Yoshiharu Iwabuchi, Naoki Kanoh

    CHEMBIOCHEM 12 (18) 2748-2752 2011/12

    DOI: 10.1002/cbic.201100541  

    ISSN: 1439-4227

  123. 9-Azanoradamantane N-Oxyl (Nor-AZADO): A Highly Active Organocatalyst for Alcohol Oxidation Peer-reviewed

    Masaki Hayashi, Yusuke Sasano, Shota Nagasawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN 59 (12) 1570-1573 2011/12

    DOI: 10.1248/cpb.59.1570  

    ISSN: 0009-2363

  124. Detection of Cytochrome P450 Substrates by Using a Small-Molecule Droplet Array on an NADH-Immobilized Solid Surface Peer-reviewed

    Hiroshi Takayama, Shunji Takahashi, Takashi Moriya, Hiroyuki Osada, Yoshiharu Iwabuchi, Naoki Kanoh

    CHEMBIOCHEM 12 (18) 2748-2752 2011/12

    DOI: 10.1002/cbic.201100541  

    ISSN: 1439-4227

  125. Practical Preparation Methods for Highly Active Azaadamantane-Nitroxyl-Radical-Type Oxidation Catalysts Peer-reviewed

    Masatoshi Shibuya, Yusuke Sasano, Masaki Tomizawa, Toshimasa Hamada, Masami Kozawa, Noriaki Nagahama, Yoshiharu Iwabuchi

    SYNTHESIS-STUTTGART (21) 3418-3425 2011/11

    DOI: 10.1055/s-0030-1260257  

    ISSN: 0039-7881

  126. Novel Curcumin Analogs, GO-Y030 and GO-Y078, Are Multitargeted Agents with Enhanced Abilities for Multiple Myeloma Peer-reviewed

    Chieko Kudo, Hiroyuki Yamakoshi, Atsuko Sato, Hisatsugu Ohori, Chikashi Ishioka, Yoshiharu Iwabuchi, Hiroyuki Shibata

    ANTICANCER RESEARCH 31 (11) 3719-3726 2011/11

    ISSN: 0250-7005

  127. Highly active organocatalyst for oxidation of alcohols Peer-reviewed

    Masaki Hayashi, Yoshiharu Iwabuchi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 242 2011/08

    ISSN: 0065-7727

  128. Targeting colon cancer stem cells using a new curcumin analogue, GO-Y030

    L. Lin, Y. Liu, H. Li, P-K Li, J. Fuchs, H. Shibata, Y. Iwabuchi, J. Lin

    BRITISH JOURNAL OF CANCER 105 (2) 212-220 2011/07

    DOI: 10.1038/bjc.2011.200  

    ISSN: 0007-0920

  129. High-performance liquid chromatography with photodiode array detection for determination of nobiletin content in the brain and serum of mice administrated the natural compound Peer-reviewed

    Daisuke Saigusa, Masatoshi Shibuya, Daisuke Jinno, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi, Akihito Yokosuka, Yoshihiro Mimaki, Akira Naganuma, Yasushi Ohizumi, Yoshihisa Tomioka, Tohru Yamakuni

    ANALYTICAL AND BIOANALYTICAL CHEMISTRY 400 (10) 3635-3641 2011/07

    DOI: 10.1007/s00216-011-5031-2  

    ISSN: 1618-2642

    eISSN: 1618-2650

  130. Concise Entry to Both Enantiomers of 8-Oxabicyclo[3.2.1]oct-3-en-2-one Based on Novel Oxidative Etherification: Formal Synthesis of (+)-Sundiversifolide Peer-reviewed

    Muneo Kawasumi, Naoki Kanoh, Yoshiharu Iwabuchi

    ORGANIC LETTERS 13 (14) 3620-3623 2011/07

    DOI: 10.1021/ol201273b  

    ISSN: 1523-7060

    eISSN: 1523-7052

  131. Asymmetric Total Synthesis of (-)-Scabronine G via Intramolecular Double Michael Reaction and Prins Cyclization Peer-reviewed

    Naoki Kanoh, Kohei Sakanishi, Emiko Iimori, Ken'ichi Nishimura, Yoshiharu Iwabuchi

    ORGANIC LETTERS 13 (11) 2864-2867 2011/06

    DOI: 10.1021/ol200873y  

    ISSN: 1523-7060

  132. Synthesis of 86 species of 1,5-diaryl-3-oxo-1,4-pentadienes analogs of curcumin can yield a good lead in vivo

    Chieko Kudo, Hiroyuki Yamakoshi, Atsuko Sato, Hiroshi Nanjo, Hisatsugu Ohori, Chikashi Ishioka, Yoshiharu Iwabuchi, Hiroyuki Shibata

    BMC Pharmacology 11 2011/05/28

    DOI: 10.1186/1471-2210-11-4  

    ISSN: 1471-2210

  133. Curcumin analog GO-Y030 is a novel inhibitor of IKK beta that suppresses NF-kappa B signaling and induces apoptosis Peer-reviewed

    Atsuko Sato, Chieko Kudo, Hiroyuki Yamakoshi, Yoshihiko Uehara, Hisatsugu Ohori, Chikashi Ishioka, Yoshiharu Iwabuchi, Hiroyuki Shibata

    CANCER SCIENCE 102 (5) 1045-1051 2011/05

    DOI: 10.1111/j.1349-7006.2011.01886.x  

    ISSN: 1347-9032

  134. Highly Efficient, Organocatalytic Aerobic Alcohol Oxidation Peer-reviewed

    Masatoshi Shibuya, Yuji Osada, Yusuke Sasano, Masaki Tomizawa, Yoshiharu Iwabuchi

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 133 (17) 6497-6500 2011/05

    DOI: 10.1021/ja110940c  

    ISSN: 0002-7863

  135. HPLC/PDA法を用いた体内動態解析による抗アルツハイマー病天然薬物ノビレチンの脳内移行の証明

    三枝 大輔, 中島 晶, 鐵 尚美, 澁谷 正俊, 山越 博幸, 岩渕 好治, 横須賀 章人, 指田 豊, 三巻 祥浩, 永沼 章, 大泉 康, 富岡 佳久

    日本薬学会年会要旨集 131年会 (4) 139-139 2011/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  136. 生体内transアコニット酸生成機構解明のための有機酸高感度定量法の確立

    松本 周平, 三枝 大輔, 竹田 千尋, 鈴木 直人, 澁谷 正俊, 岩渕 好治, 富岡 佳久

    日本薬学会年会要旨集 131年会 (4) 288-288 2011/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  137. Irciniastatin A induces JNK activation that is involved in caspase-8-dependent apoptosis via the mitochondrial pathway Peer-reviewed

    Takumi Chinen, Yoko Nagumo, Tsubasa Watanabe, Takamichi Imaizumi, Masatoshi Shibuya, Takao Kataoka, Naoki Kanoh, Yoshiharu Iwabuchi, Takeo Usui

    TOXICOLOGY LETTERS 199 (3) 341-346 2010/12

    DOI: 10.1016/j.toxlet.2010.09.017  

    ISSN: 0378-4274

    eISSN: 1879-3169

  138. Concise Total Synthesis of Vicenistatin Peer-reviewed

    Hayato Fukuda, Shiina Nakamura, Tadashi Eguchi, Yoshiharu Iwabuchi, Naoki Kanoh

    SYNLETT (17) 2589-2592 2010/10

    DOI: 10.1055/s-0030-1258574  

    ISSN: 0936-5214

  139. AN ENANTIO- AND DIASTEREOCONTROLLED SYNTHESIS OF (-)-SALINOSPORAMIDE A Peer-reviewed

    Yosuke Sato, Hayato Fukuda, Masaki Tomizawa, Tomohito Masaki, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

    HETEROCYCLES 81 (10) 2239-2246 2010/10

    DOI: 10.3987/COM-10-12042  

    ISSN: 0385-5414

    eISSN: 1881-0942

  140. KSRP/FUBP2 Is a Binding Protein of GO-Y086, a Cytotoxic Curcumin Analogue Peer-reviewed

    Hiroyuki Yamakoshi, Naoki Kanoh, Chieko Kudo, Atsuko Sato, Kazunori Ueda, Makoto Muroi, Shunsuke Kon, Masanobu Satake, Hisatsugu Ohori, Chikashi Ishioka, Yoshiteru Oshima, Hiroyuki Osada, Natsuko Chiba, Hiroyuki Shibata, Yoshiharu Iwabuchi

    ACS MEDICINAL CHEMISTRY LETTERS 1 (6) 273-276 2010/09

    DOI: 10.1021/ml1000454  

    ISSN: 1948-5875

  141. Total Synthesis and Determination of the Absolute Configuration of (-)-Idesolide Peer-reviewed

    Hiroyuki Yamakoshi, Masatoshi Shibuya, Masaki Tomizawa, Yuji Osada, Naoki Kanoh, Yoshiharu Iwabuchi

    ORGANIC LETTERS 12 (5) 980-983 2010/03

    DOI: 10.1021/ol9029676  

    ISSN: 1523-7060

    eISSN: 1523-7052

  142. Syntheses and Biological Evaluation of Irciniastatin A and the C1-C2 Alkyne Analogue Peer-reviewed

    Tsubasa Watanabe, Takamichi Imaizumi, Takumi Chinen, Yoko Nagumo, Masatoshi Shibuya, Takeo Usui, Naoki Kanoh, Yoshiharu Iwabuchi

    ORGANIC LETTERS 12 (5) 1040-1043 2010/03

    DOI: 10.1021/ol1000389  

    ISSN: 1523-7060

    eISSN: 1523-7052

  143. Structure-activity relationship of C-5-curcuminoids and synthesis of their molecular probes thereof Peer-reviewed

    Hiroyuki Yamakoshi, Hisatsugu Ohori, Chieko Kudo, Atsuko Sato, Naoki Kanoh, Chikashi Ishioka, Hiroyuki Shibata, Yoshiharu Iwabuchi

    BIOORGANIC & MEDICINAL CHEMISTRY 18 (3) 1083-1092 2010/02

    DOI: 10.1016/j.bmc.2009.12.045  

    ISSN: 0968-0896

    eISSN: 1464-3391

  144. Cleavable Linker for Photo-Cross-Linked Small-Molecule Affinity Matrix Peer-reviewed

    Naoki Kanoh, Hiroshi Takayama, Kaori Honda, Takashi Moriya, Takayuki Teruya, Siro Simizu, Hiroyuki Osada, Yoshiharu Iwabuchi

    BIOCONJUGATE CHEMISTRY 21 (1) 182-186 2010/01

    DOI: 10.1021/bc900316q  

    ISSN: 1043-1802

  145. Curcumin analogue GO-Y030 inhibits STAT3 activity and cell growth in breast and pancreatic carcinomas

    Brian Hutzen, Lauren Friedman, Matthew Sobo, Li Lin, Ling Cen, Stephanie De Angelis, Hiroyuki Yamakoshi, Hiroyuki Shibata, Yoshiharu Iwabuchi, Jiayuh Lin

    INTERNATIONAL JOURNAL OF ONCOLOGY 35 (4) 867-872 2009/10

    DOI: 10.3892/ijo_00000401  

    ISSN: 1019-6439

    eISSN: 1791-2423

  146. Curcumin analogue GO-Y030 inhibits STAT3 activity and cell growth in breast and pancreatic carcinomas Peer-reviewed

    Brian Hutzen, Lauren Friedman, Matthew Sobo, Li Lin, Ling Cen, Stephanie De Angelis, Hiroyuki Yamakoshi, Hiroyuki Shibata, Yoshiharu Iwabuchi, Jiayuh Lin

    INTERNATIONAL JOURNAL OF ONCOLOGY 35 (4) 867-872 2009/10

    DOI: 10.3892/ijo_00000401  

    ISSN: 1019-6439

    eISSN: 1791-2423

  147. An Expedient Route to a Potent Gastrin/CCK-B Receptor Antagonist (+)-AG-041R Peer-reviewed

    Shigeki Sato, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 74 (19) 7522-7524 2009/10

    DOI: 10.1021/jo901352u  

    ISSN: 0022-3263

  148. 4 '-Demethylnobiletin, a Bioactive Metabolite of Nobiletin Enhancing PKA/ERK/CREB Signaling, Rescues Learning Impairment Associated with NMDA Receptor Antagonism via Stimulation of the ERK Cascade Peer-reviewed

    Md Al Rahim, Akira Nakajima, Daisuke Saigusa, Naomi Tetsu, Yuji Maruyama, Masatoshi Shibuya, Hiroyuki Yamakoshi, Yoshihisa Tomioka, Yoshiharu Iwabuchi, Yasushi Ohizumi, Tohru Yamakuni

    BIOCHEMISTRY 48 (32) 7713-7721 2009/08

    DOI: 10.1021/bi901088w  

    ISSN: 0006-2960

  149. An Expeditious Entry to 9-Azabicyclo[3.3.1]nonane N-Oxyl (ABNO): Another Highly Active Organocatalyst for Oxidation of Alcohols Peer-reviewed

    Masatoshi Shibuya, Masaki Tomizawa, Yusuke Sasano, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 74 (12) 4619-4622 2009/06

    DOI: 10.1021/jo900486w  

    ISSN: 0022-3263

  150. Newly synthesized curcumin analog has improved potential to prevent colorectal carcinogenesis in vivo Peer-reviewed

    Hiroyuki Shibata, Hiroyuki Yamakoshi, Atsuko Sato, Hisatsugu Ohori, Yuichi Kakudo, Chieko Kudo, Yayoi Takahashi, Mika Watanabe, Hiroshi Takano, Chikashi Ishioka, Tetsuo Noda, Yoshiharu Iwabuchi

    CANCER SCIENCE 100 (5) 956-960 2009/05

    DOI: 10.1111/j.1349-7006.2009.01127.x  

    ISSN: 1347-9032

  151. Therapeutic potential of newly synthesized curcumin analogs Peer-reviewed

    Hiroyuki Shibata, Chieko Kudo, Atsuko Sato, Hisatsugu Ohori, Hiroyuki Yamakoshi, Chikashi Ishioka, Yoshiharu Iwabuchi

    CANCER RESEARCH 69 2009/05

    ISSN: 0008-5472

    eISSN: 1538-7445

  152. Synthetic Studies on Daphnicyclidin A: Enantiocontrolled Construction of the BCD Ring System Peer-reviewed

    Shuhei Ikeda, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

    ORGANIC LETTERS 11 (8) 1833-1836 2009/04

    DOI: 10.1021/ol9003405  

    ISSN: 1523-7060

    eISSN: 1523-7052

  153. Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chirally Modified AZADOs Peer-reviewed

    Masaki Tomizawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

    ORGANIC LETTERS 11 (8) 1829-1831 2009/04

    DOI: 10.1021/ol900441f  

    ISSN: 1523-7060

    eISSN: 1523-7052

  154. FLEXIBLE ACCESS TO MONOTERPENOID INDOLE ALKALOIDS USING A CYCLOPENTANOID CHIRAL BUILDING BLOCK Peer-reviewed

    Masato Hayashi, Keiichi Motosawa, Atsushi Satoh, Masatoshi Shibuya, Kunio Ogasawara, Yoshiharu Iwabuchi

    HETEROCYCLES 77 (2) 855-863 2009/02

    DOI: 10.3987/COM-08-S(F)120  

    ISSN: 0385-5414

    eISSN: 1881-0942

  155. Activation of Endothelial Nitric Oxide Synthase by a Vanadium Compound Ameliorates Pressure Overload-Induced Cardiac Injury in Ovariectomized Rats Peer-reviewed

    Shenuarin Bhuiyan, Norifumi Shioda, Masatoshi Shibuya, Yoshiharu Iwabuchi, Kohji Fukunaga

    HYPERTENSION 53 (1) 57-63 2009/01

    DOI: 10.1161/HYPERTENSIONAHA.108.118356  

    ISSN: 0194-911X

    eISSN: 1524-4563

  156. Oxoammonium salt/NaClO2: an expedient, catalytic system for one-pot oxidation of primary alcohols to carboxylic acids with broad substrate applicability Peer-reviewed

    Masatoshi Shibuya, Takahisa Sato, Masaki Tomizawa, Yoshiharu Iwabuchi

    CHEMICAL COMMUNICATIONS (13) 1739-1741 2009

    DOI: 10.1039/b822944a  

    ISSN: 1359-7345

    eISSN: 1364-548X

  157. Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity Peer-reviewed

    Hiroyuki Yamakoshi, Fumiya Ikarashi, Masataka Minami, Masatoshi Shibuya, Tsutomu Sugahara, Naoki Kanoh, Hisatsugu Ohori, Hiroyuki Shibata, Yoshiharu Iwabuchi

    ORGANIC & BIOMOLECULAR CHEMISTRY 7 (18) 3772-3781 2009

    DOI: 10.1039/b909646a  

    ISSN: 1477-0520

    eISSN: 1477-0539

  158. Highly enantioselective intramolecular aza-spiroannulation onto indoles using chiral rhodium catalysis: asymmetric entry to the spiro-beta-lactam core of chartellines Peer-reviewed

    Shigeki Sato, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

    CHEMICAL COMMUNICATIONS (41) 6264-6266 2009

    DOI: 10.1039/b913770j  

    ISSN: 1359-7345

    eISSN: 1364-548X

  159. Exploration and Exploitation of Synthetic Use of Oxoammonium Ions in Alcohol Oxidation Peer-reviewed

    Yoshiharu Iwabuchi

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 66 (11) 1076-1084 2008/11

    DOI: 10.5059/yukigoseikyokaishi.66.1076  

    ISSN: 0037-9980

  160. TEMPO/NalO(4)-SiO2: A Catalytic Oxidative Rearrangement of Tertiary Allylic Alcohols to beta-Substituted alpha,beta-Unsaturated Ketones Peer-reviewed

    Masatoshi Shibuya, Masaki Tomizawa, Yoshiharu Iwabuchi

    ORGANIC LETTERS 10 (21) 4715-4718 2008/11

    DOI: 10.1021/ol801673r  

    ISSN: 1523-7060

  161. Efficient Entry to the Pyrroloquinoline Core of Martinella Alkaloids via Novel Base-catalyzed Mukaiyama-Mannich Reaction Peer-reviewed

    Shuhei Ikeda, Masatoshi Shibuya, Naoki Kanoh, Yoshiharu Iwabuchi

    CHEMISTRY LETTERS 37 (9) 962-963 2008/09

    DOI: 10.1246/cl.2008.962  

    ISSN: 0366-7022

    eISSN: 1348-0715

  162. Distribution of photo-cross-linked products from 3-aryl-3-trifluoromethyldiazirines and alcohols Peer-reviewed

    Naoki Kanoh, Takemichi Nakamura, Kaori Honda, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi, Hiroyuki Osada

    TETRAHEDRON 64 (24) 5692-5698 2008/06

    DOI: 10.1016/j.tet.2008.04.031  

    ISSN: 0040-4020

  163. Oxidative rearrangement of tertiary allylic alcohols employing oxoammonium salts Peer-reviewed

    Masatoshi Shibuya, Masaki Tomizawa, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 73 (12) 4750-4752 2008/06

    DOI: 10.1021/jo800634r  

    ISSN: 0022-3263

  164. Chemoenzymatic preparation of functionalized bicyclo[3.2.1]octenone and practical utilization Peer-reviewed

    Shinichiro Ito, Ayako Tosaka, Keisuke Hanada, Masatoshi Shibuya, Kunio Ogasawara, Yoshiharu Iwabuchi

    TETRAHEDRON-ASYMMETRY 19 (2) 176-+ 2008/02

    DOI: 10.1016/j.tetasy.2007.12.009  

    ISSN: 0957-4166

  165. Neuroprotective effect of a vanadium compound and melatonin in MPTP-induced dopaminergic defects in mice Peer-reviewed

    Jiro Kasahara, Tomofumi Nagai, Masatoshi Shibuya, Yoshiharu Iwabuchi, Norie Araki, Kohji Fukunaga

    NEUROSCIENCE RESEARCH 61 S265-S265 2008

    ISSN: 0168-0102

  166. Cytoprotective effect of bis(1-oxy-2-pyridinethiolato)oxovanadiun(IV) on myocardial ischemia/reperfusion injury elicits inhibition of Fas ligand and Bim expression and elevation of FLIP expression

    Md. Shenuarin Bhuiyan, Masatoshi Shibuya, Norifumi Shioda, Shigeki Moriguchi, Jiro Kasahara, Yosiharu Iwabuchi, Kohji Fukunaga

    EUROPEAN JOURNAL OF PHARMACOLOGY 571 (2-3) 180-188 2007/10

    DOI: 10.1016/j.ejphar.2007.05.046  

    ISSN: 0014-2999

  167. 25 Asymmetric Total Synthesis of Martinella Alkaloids

    Ikeda Shuhei, Shibuya Masatoshi, Iwashita Masaya, Saitoh Masaki, Nakahata Norimichi, Iwabuchi Yoshiharu

    Symposium on the Chemistry of Natural Products, symposium papers (49) 145-150 2007/08/24

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.49.0_145  

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    Due to the novel hexahydropyrrolo[3,2-c]quinoline nucleus as well as their potential use in medicinal chemistry, martinelline (1) and martinellic acid (2), isolated from the root bark of the tropical plant Martinella iquitosensis, have spurred intense efforts to synthesize them. Although there have been reported several total syntheses, the issue on the elucidation of the absolute configurations of 1 and 2 is still the subject of serious arguments. In addition, there have been reported few methodologies that allow facile construction of the tricyclic core in an enantiocontrolled manner. Herein, we describe the first asymmetric total synthesis of (-)-martinelline (1) and the second total synthesis of (-)-martinellic acid (2) based on the highly efficient Lewis base-promoted intramolecular Mukaiyama-Mannich/hemiaminalization reaction using imine 18. Unexpectedly, a comparison of their specific rotations suggested that the reported natural Martinella alkaloids are nearly racemic or mixtures of two enantiomers. To determine which of the two enantiomers confers biological activities, both enantiomers were also synthesized. Evaluation of the GPCR antagonist activity toward H_1-hiatamine receptors on human astrocytoma 1321N1 cells revealed that only (-)-(3aS,4S,9bS)-martinelline (1) exhibits GPCR antagonist activity.

  168. Activation of phosphatidylinositol 3-kinase/protein kinase B pathway by a vanadyl compound mediates its neuroprotective effect in mouse brain ischemia

    N. Shioda, T. Ishigami, F. Han, S. Moriguchi, M. Shibuya, Y. Iwabuchi, K. Fukunag

    NEUROSCIENCE 148 (1) 221-229 2007/08

    DOI: 10.1016/j.neuroscience.2007.05.040  

    ISSN: 0306-4522

  169. Synthesis of an enantiomeric DNA oligomer and its T-HgII-T base-pair formation.

    Kaichiro Haruta, Yoshiyuki Tanaka, Takuya Kawamura, Yoshinori Kondo, Akira Ono, Hiroyuki Yamakoshi, Naoki Kanoh, Yoshiharu Iwabuchi

    Nucleic acids symposium series (2004) 187-188 2007/01/01

  170. Asymmetric total synthesis of martinelline and martinellic acid Peer-reviewed

    Shuhei Ikeda, Masatoshi Shibuya, Yoshiharu Iwabuchi

    CHEMICAL COMMUNICATIONS (5) 504-506 2007

    DOI: 10.1039/b611121a  

    ISSN: 1359-7345

  171. Enantio- and diastereocontrolled synthesis of (+)-juvabione employing organocatalytic desymmetrisation and photoinduced fragmentation Peer-reviewed

    Noriaki Itagaki, Yoshiharu Iwabuchi

    CHEMICAL COMMUNICATIONS (11) 1175-1176 2007

    DOI: 10.1039/b616641e  

    ISSN: 1359-7345

  172. Protective effects of nobiletin and its derivative on NMDA receptor antagonist MK-801-induced learning and memory deficits in mice. Peer-reviewed

    Akira Nakajima, Tohru Yamakuni, Yuji Maruyama, Kentaro Matsuzaki, Masatoshi Shibuya, Yoshiharu Iwabuchi, Akihito Yokosuka, Yutaka Sashida, Yoshihiro Mimaki, Yasushi Ohizumi

    JOURNAL OF PHARMACOLOGICAL SCIENCES 103 179P-179P 2007

    ISSN: 1347-8613

  173. Total synthesis of (-)-dihydrocorynantheol using bicyclo[3.2.1]octenone chiral building block Peer-reviewed

    Ayako Tosaka, Shinichiro Ito, Norio Miyazawa, Masatoshi Shibuya, Kunio Ogasawara, Yoshiharu Iwabuchi

    HETEROCYCLES 70 153-+ 2006/12

    DOI: 10.3987/COM-06-S(W)49  

    ISSN: 0385-5414

    eISSN: 1881-0942

  174. Synthesis and biological analysis of new curcumin analogues bearing an enhanced potential for the medicinal treatment of cancer Peer-reviewed

    Hisatsugu Ohori, Hiroyuki Yamakoshi, Masaki Tomizawa, Masatoshi Shibuya, Yuichi Kakudo, Atsuko Takahashi, Shin Takahashi, Satoshi Kato, Takao Suzuki, Chikashi Ishioka, Yoshiharu Iwabuchi, Hiroyuki Shibata

    MOLECULAR CANCER THERAPEUTICS 5 (10) 2563-2571 2006/10

    DOI: 10.1158/1535-7163.MCT-06-0174  

    ISSN: 1535-7163

  175. P-116 The Asymmetric Total Synthesis of Martinelline

    Ikeda Shuhei, Sugawara Tsuyoshi, Shibuya Masatoshi, Iwabuchi Yoshiharu

    International Symposium on the Chemistry of Natural Products 2006 "P-116" 2006/07/23

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/intnaturalprod.2006.0__P-116_  

  176. 2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO: Highly efficient organocatalysts for oxidation of alcohols Peer-reviewed

    Masatoshi Shibuya, Masaki Tomizawa, Iwao Suzuki, Yoshiharu Iwabuchi

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 128 (26) 8412-8413 2006/07

    DOI: 10.1021/ja0620336  

    ISSN: 0002-7863

  177. Identification and possibility of new curcumin analogs bearing the dual enhanced potentials for the degradation of oncoproteins and the stabilization of p53

    Hisatsugu Ohori, Hiroyuki Shibata, Yuichi Kakudo, Atsuko Maeda, Yoshiharu Iwabuchi, Chikashi Ishioka

    CANCER RESEARCH 66 (8) 2006/04

    ISSN: 0008-5472

    eISSN: 1538-7445

  178. An enantio- and diastereocontrolled synthesis of (+)-7-deoxy-trans-dihydronarciclasine (PII:S0385-5414(05)80388-0)

    Takashi Fujimura, Masatoshi Shibuya, Kunio Ogasawara, Yoshiharu Iwabuchi

    Heterocycles 68 451 2006/02/01

    ISSN: 0385-5414

  179. beta-isocupreidine-hexafluoroisopropyl acrylate method for asymmetric Baylis-Hillman reactions

    A Nakano, S Kawahara, S Akamatsu, K Morokuma, M Nakatani, Y Iwabuchi, K Takahashi, J Ishihara, S Hatakeyama

    TETRAHEDRON 62 (2-3) 381-389 2006/01

    DOI: 10.1016/j.tet.2005.09.072  

    ISSN: 0040-4020

  180. An enantio- and diastereocontrolled synthesis of (+)-7deoxy-trans-dihydronarciclasine

    T Fujimura, M Shibuya, K Ogasawara, Y Iwabuchi

    HETEROCYCLES 66 167-173 2005/12

    DOI: 10.3987/COM-05-S(K)68  

    ISSN: 0385-5414

  181. Synthesis of an enantiocomplementary catalyst of beta-isocupreidine (beta-ICD) from quinine

    A Nakano, M Ushiyama, Y Iwabuchi, S Hatakeyama

    ADVANCED SYNTHESIS & CATALYSIS 347 (14) 1790-1796 2005/11

    DOI: 10.1002/adsc.200505138  

    ISSN: 1615-4150

  182. Erratum: Expedient synthesis of potent cannabinoid receptor agonist (Organic Letters) (4181-4183)

    Noriaki Itagaki, Tsutomu Sugahara, Yoshiharu Iwabuchi

    Organic Letters 7 4785 2005/10/13

    ISSN: 1523-7060

  183. P-50 Studies toward Total Synthesis of (+)-Martinelline

    Ikeda Shuhei, Shibuya Masatoshi, Iwabuchi Yoshiharu

    Symposium on the Chemistry of Natural Products, symposium papers (47) 589-594 2005/09/15

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.47.0_589  

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    Martinelline (1) and martinellic acid (2) were isolated by Witherup et al. at Merck Resarch Laboratories from the roots of the South American plant Martinella iquitosensis. These are the first naturally occurring non-peptide bradykinin B_1 and B_2 receptor antagonist, and are the first alkaloids with the hexahydropyrrolo[3,2-c]quinoline ring system. The biological activities of 1 and 2 coupled with their intriguing molecular frame have spurred intense synthetic efforts which culminated in the several total syntheses. To date, however, there have been reported a limited number of methodologies that allow facile construction of the tricyclic core in an enantiocontrolled manner. We envisaged a convergent route, involving an intramolecular hetero Diels-Alder reaction of an o-quinone methide imide formed in situ via isomerization of an imine. After considerable experimentations, we eventually found that LiBF_4 promoted conversion of TBS enol ether 12c to furnish pyrrolo[3,2-c]quinoline 14 as a single stereoisomer in a moderate yield, probably via a stepwise sequence involving an iminium ion intermediate but not via the expected concerted manner. Adduct 16, derived from an advanced building block 17, was successfully transformed into the known intermediate 23 through a diastereoselective Hosomi-Sakurai allylation and a set of conventional functional group transformations, thereby establishing the stereoselectivity of the key [4+2]-cyclization. We then applied this cycloisomerization reaction to a chiral substrate 24 having TBDPSoxymethyl group as a stereocontrolling element. It was found that BF_3・OEt_2 worked nicely in this particular case to give two diastereoisomers in a moderate yield with a 33: 9 ratio, in which the major isomer was confirmed to possess the suitable stereochemistries for synthesis of (+)-martinelline.

  184. Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization

    N Itagaki, M Kimura, T Sugahara, Y Iwabuchi

    ORGANIC LETTERS 7 (19) 4185-4188 2005/09

    DOI: 10.1021/ol051569d  

    ISSN: 1523-7060

  185. Expedient synthesis of potent cannabinoid receptor agonist (-)-CP55,940

    N Itagaki, T Sugahara, Y Iwabuchi

    ORGANIC LETTERS 7 (19) 4181-4183 2005/09

    DOI: 10.1021/ol051570c  

    ISSN: 1523-7060

  186. Oxidative rearrangement of cyclic tertiary allylic alcohols with IBX in DMSO Peer-reviewed

    M Shibuya, S Ito, M Takahashi, Y Iwabuchi

    ORGANIC LETTERS 6 (23) 4303-4306 2004/11

    DOI: 10.1021/ol048210u  

    ISSN: 1523-7060

  187. 78(P-75) Synthetic Studies of Antitumor Cylindrocyclophanes

    Minami Masataka, Sugahara Tsutomu, Iwabuchi Yosiharu

    Symposium on the Chemistry of Natural Products, symposium papers (46) 443-448 2004/10/01

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.46.0_443  

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    [7.7] Paracyclophanes, cylindrocyclophanes (A〜F,1-6) and nostocyclophane D (7), are a new class of macrocyclic compounds isolated from blue-green algae, Cylindrospermum licheniforme and Nostoc linckia, by Moore, et al. in 1990. These 22-membered cyclophanes exhibit potent antitumor activity. The enantioselective syntheses of cylindrocyclophane A (1) have already reported by Smith, et al. and Hoye,et al., respectively. However, the structure-activity relationship of cyclophanes is not clear. Therefore, we designed new, convergent synthetic routes to prepare cylindrocyclophane A (1) and its derivatives to address the above mentioned problems. We report herein our formal total synthesis of cylindrocyclophane A (1). Syringaldehyde (15) was transformed into triflate 16 for the three steps. (E)-Stannylalkene 18 was obtained from propargyl alcohol 17 which was synthesized from (+)-diethyl tartrate by the known procedures. By the Stille coupling reaction of (E)-Stannylalkene 18 with triflate 16 followed by the Johnson-Claisen rearrangement, ester 20 was obtained, which was constructed the chiral center at C-20 of cylindrocyclophane A (1). The ester 20 was transformed into olefin 23 for the five steps. The chiral centers at C-1 and C-2 were constructed through the Evans asymmetric aldol reaction of aldehyde 24, which was obtained from olefin 23, and oxazolidinone 25. The coupling product 26 was transformed into important intermediate 28, which was synthesized by Smith, et al. for the synthesis of cylindrocyclophane A (1). The synthesized diolefin 28 was identical with the reported 28 in all spectroscopic properties. Further studies toward the total syntheses of cylindrocyclophane A (1) and cylindrocyclophane's derivatives are now under way using catalytic olefin cross methathesis.

  188. A concise route to (+)-lactacystin Peer-reviewed

    H Ooi, N Ishibashi, Y Iwabuchi, J Ishihara, S Hatakeyama

    JOURNAL OF ORGANIC CHEMISTRY 69 (22) 7765-7768 2004/10

    DOI: 10.1021/jo048817o  

    ISSN: 0022-3263

  189. Total synthesis and absolute stereochemistry of pentenocin B, a novel interleukin-1 beta converting enzyme inhibitor Peer-reviewed

    T Sugahara, H Fukuda, Y Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY 69 (5) 1744-1747 2004/03

    DOI: 10.1021/jo035430x  

    ISSN: 0022-3263

  190. A diastereocontrolled synthesis of perseitol using a dioxabicyclo[3.2.1]octane chiral building block

    Kohei Kadota, Kunio Ogasawara, Yoshiharu Iwabuchi

    Arkivoc 2003 163-170 2003/12/01

    ISSN: 1424-6376

  191. 97(P-30) Synthesis and Determination of the Absolute Configurations of Pentenocins, Novel Inhibitors of Caspase-1

    Sugahara Tsutomu, Fukuda Hayato, Iwabuchi Yoshiharu

    Symposium on the Chemistry of Natural Products, symposium papers (45) 573-578 2003/09/01

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.45.0_573  

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    Pentenocins A (1) and B (2) were isolated by Omura et al. in 1999. The planar structures of 1 and 2 were determined by NMR spectral analysis, however, the relative and absolute configurations of these cyclopentenones were not elucidated. We report here the syntheses of the four possible racemic pentenocins B 3〜6 and the first synthesis of (+)-pentenocin B, and the determination of the relative and absolute configurations of natural pentenocin B. We synthesized the four possible racemic pentenocins B 3〜6 to determine the relative configuration of pentenocin B using racemic ketodicyclopentadiene (KDP) 8 as the common starting material. 8 was converted to the 1,4-diols 10a and 10b as an 86:14 mixture of diastereomers. Although the configurations of the diastereomers 10a and 10b were not determined, the major alcohol of 10a was transformed to the ketone 13a. The retro Diels-Alder reaction of 13a was performed to the cyclopentenone 14a. Finally, 14a was treated with 90% TFA to give (±)-pentenocin B 3 or 4. The minor alcohol 10b was transformed to (±)-pentenocin B 4 or 3 by the same procedures as those for the major alcohol 10a to (±)-pentenocin B 3 or 4. To synthesize (±)-pentenocin B 5 or 6, the mixture of the 1,4-diols 10a and 10b was converted to the α,β-unsaturated ketones 18a and 18b via a Wharton rearrangement. 18a was then converted to (±)-pentenocin B 5. The Z-isomer 18b was transformed to (±)-pentenocin B 6 by the same procedures as those for 18a to 5. The NMR spectrum of synthetic pentenocin B 3 or 4 from the major alcohol 10a was in agreement with those of natural pentenocin B from the comparison of NMR spectra between reported natural pentenocin B and synthetic (±)-pentenocins B 3〜6. Having secured the diastereoselective route to pentenocin B, we then conducted the enantioselective synthesis to determine the absolute stereochemistry of natural pentenocin B. (-)-KDP 8 was transformed to (+)-pentenocin B 3 as shown in scheme 4 with the same procedures as described for the synthesis of the racemic pentenocin B 3 or 4. The (R)-stereochemistry of the C-6 secondary alcohol in (+)-pentenocin B 3 was determined using the modified Mosher method and the X-ray analysis. We then developed new synthetic routes to (+)-pentenocin B 3 from (-)-KDP 8 as shown in the scheme 5 to improve the synthetic yield. In conclusion, we have realized the first enantiocontrolled synthesis of (+)-pentenocin B and determined its absolute stereochemistry to be 4S,5R,6R as compared with the value of optical rotation with natural pentenocin B.

  192. beta-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines Peer-reviewed

    S Kawahara, A Nakano, T Esumi, Y Iwabuchi, S Hatakeyama

    ORGANIC LETTERS 5 (17) 3103-3105 2003/08

    DOI: 10.1021/ol035102j  

    ISSN: 1523-7060

  193. Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration

    K Hirai, H Ooi, T Esumi, Y Iwabuchi, S Hatakeyama

    ORGANIC LETTERS 5 (6) 857-859 2003/03

    DOI: 10.1021/ol0275264  

    ISSN: 1523-7060

  194. A diastereocontrolled synthesis of perseitol using a dioxabicyclo[3.2.1]octane chiral building block Invited Peer-reviewed

    K Kadota, K Ogasawara, Y Iwabuchi

    ARKIVOC (8) 163-170 2003

    ISSN: 1551-7004

  195. Potent antimalarial febrifugine analogues against the Plasmodium malaria parasite

    H Kikuchi, H Tasaka, S Hirai, Y Takaya, Y Iwabuchi, H Ooi, S Hatakeyama, HS Kim, Y Wataya, Y Oshima

    JOURNAL OF MEDICINAL CHEMISTRY 45 (12) 2563-2570 2002/06

    DOI: 10.1021/jm010448q  

    ISSN: 0022-2623

  196. Fluorescent cytochemical detection of sialidase activity using 5-bromo-4-chloroindol-3-yl-alpha-D-N-acetylneuraminic acid as the substrate

    M Saito, H Hagita, Y Iwabuchi, Fujii, I, K Ikeda, M Ito

    HISTOCHEMISTRY AND CELL BIOLOGY 117 (5) 453-458 2002/05

    DOI: 10.1007/s00418-002-0399-x  

    ISSN: 0948-6143

  197. Recent progress in the Morita-Baylis-Hillman reactions

    Y Iwabuchi, S Hatakeyama

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 60 (1) 2-14 2002/01

    DOI: 10.5059/yukigoseikyokaishi.60.2  

    ISSN: 0037-9980

  198. An enantio- and stereocontrolled route to epopromycin B via cinchona alkaloid-catalyzed Baylis-Hillman reaction Peer-reviewed

    Yoshiharu Iwabuchi, Tatsuya Sugihara, Tomoyuki Esumi, Susumi Hatakeyama

    Tetrahedron Letters 42 (44) 7867-7871 2001/10/29

    DOI: 10.1016/S0040-4039(01)01676-8  

    ISSN: 0040-4039

  199. An enantio- and stereocontrolled synthesis of (-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction Peer-reviewed

    Y Iwabuchi, M Furukawa, T Esumi, S Hatakeyama

    CHEMICAL COMMUNICATIONS (19) 2030-2031 2001/10

    DOI: 10.1039/b106471c  

    ISSN: 1359-7345

  200. Synthesis and biological characterization of 1α,24,25-trihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (24-hydroxylated ED-71)

    Susumi Hatakeyama, Akira Kawase, Yasushi Uchiyama, Junji Maeyama, Yoshiharu Iwabuchi, Noboru Kubodera

    Steroids 66 (3-5) 267-276 2001/05/01

    DOI: 10.1016/S0039-128X(00)00149-5  

    ISSN: 0039-128X

  201. A concise enantioselective synthesis of antimalarial febrifugine alkaloids

    H Ooi, A Urushibara, T Esumi, Y Iwabuchi, S Hatakeyama

    ORGANIC LETTERS 3 (6) 953-955 2001/03

    DOI: 10.1021/ol015655z  

    ISSN: 1523-7060

  202. A concise enantioselective synthesis of a key A-ring synthon for 1 alpha-hydroxyvitamin D-3 compounds

    H Hiyamizu, H Ooi, Y Inomoto, T Esumi, Y Iwabuchi, S Hatakeyama

    ORGANIC LETTERS 3 (3) 473-475 2001/02

    DOI: 10.1021/ol006982u  

    ISSN: 1523-7060

  203. Clinical features and alterations in the inferior horn sizes in lateral ventricle in Alzheimer's patients with different ApoE genotype in Japanese population

    Yoshiharu Iwabuchi

    Progress in Neuro-Psychopharmacology and Biological Psychiatry 2001

    DOI: 10.1016/S0278-5846(01)00199-3  

  204. Concise synthesis of (3R,4S)-3-hydroxy-4-methyl-gamma-butyrolactone

    T Nishiyama, T Nishioka, T Esumi, Y Iwabuchi, S Hatakeyama

    HETEROCYCLES 54 (1) 69-72 2001/01

    ISSN: 0385-5414

  205. Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT)

    Susumi Hatakeyama, Toshio Okano, Junji Maeyama, Tomoyuki Esumi, Hiroko Hiyamizu, Yoshiharu Iwabuchi, Kimie Nakagawa, Keiichi Ozono, Akira Kawase, Noboru Kubodera

    Bioorganic and Medicinal Chemistry 9 (2) 403-415 2001

    DOI: 10.1016/S0968-0896(00)00259-5  

    ISSN: 0968-0896

  206. 69(P-55) Exploring a New Type of Antimalarials Based on the Plant Quinazolinoid, Febrifugine

    Takaya Yoshiaki, Tasaka Hidehisa, Hirai Shingo, Oshima Yoshiteru, Iwabuchi Yoshiyasu, Hatakeyama Susumi, Kim Hye-Sook, Wataya Yusuke, Fukushima Masakazu

    Symposium on the Chemistry of Natural Products, symposium papers (42) 409-414 2000/10/01

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.42.0_409  

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    Febrifugine (1) and isofebrifugine (2), isolated from the roots of Dichroa febrifuga Lour. (Chinese name: Chang Shan) are active principles against malaria. Clinical testing of febrifugine (1) was not successful, and the results of clinical evaluation are not yet available. To reinvestigate the antimalarial activity of these compounds, and to get functional informations to exhibit the activity, we set about studying febrifugine and its analogues. Adducts of febrifugine (1) and isofebrifugine (2) with acetone, Df-1 (3) and Df-2 (4), respectively, were obtained using silica gel and acetone. They showed high activity against P. falciparum malaria in vitro. Structure-activity relationships (SAR) studies on the antimalarial activity of febrifugine-analogues revealed that 4-quinazolinone moiety along with 1'-ketone, 5'-N atom and 9'-O-function are necessary to exhibit antimalarial activity. Moreover, Df-1 (3) was found to be equally effective to P. berghei in vivo as the clinically used drug chloroquine, whereas 4 showed only 1/24 activity of 3. Whole blood concentration of Df-2 (4) decreased more rapidly than that of Df-1 (3). This finding was accounted by the metabolism studies of these compounds by using S-9 mix prepared from mouse liver. Df-2 (4) was readily metabolized in mouse liver. Accordingly, the dose of Df-2 (4) must be higher than that of Df-1 (3) to attain blood levels sufficient for a favorable therapeutic effect.

  207. Concise synthesis of anolignan A

    MM Luo, A Matsui, T Esumi, Y Iwabuchi, S Hatakeyama

    TETRAHEDRON LETTERS 41 (22) 4401-4402 2000/06

    DOI: 10.1016/S0040-4039(00)00604-3  

    ISSN: 0040-4039

  208. Stereocontrolled synthesis of (+)-lycoperdic acid based on a palladium catalyzed reaction using a serine-derived organozinc reagent

    H Masaki, T Mizozoe, T Esumi, Y Iwabuchi, S Hatakeyama

    TETRAHEDRON LETTERS 41 (24) 4801-4804 2000/06

    DOI: 10.1016/S0040-4039(00)00719-X  

    ISSN: 0040-4039

  209. Characterization of new conjugated metabolites in bile of rats administered 24,25-dihydroxyvitamin D-3 and 25-hydroxyvitamin D-3

    T Higashi, K Miura, R Kikuchi, K Shimada, H Hiyamizu, H Ooi, Y Iwabuchi, S Hatakeyama, N Kubodera

    STEROIDS 65 (5) 281-294 2000/05

    DOI: 10.1016/S0039-128X(00)00087-8  

    ISSN: 0039-128X

  210. Total synthesis of (-)-dysiherbaine

    H Masaki, J Maeyama, K Kamada, T Esumi, Y Iwabuchi, S Hatakeyama

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 122 (21) 5216-5217 2000/05

    DOI: 10.1021/ja000817s  

    ISSN: 0002-7863

  211. Enantioselective synthesis of (+)-decarestrictine L from (2E,5E)-dibenzyloxy-2,5-heptadien-4-ol

    T Esumi, R Kimura, M Mori, Y Iwabuchi, H Irie, S Hatakeyama

    HETEROCYCLES 52 (2) 525-528 2000/02

    ISSN: 0385-5414

  212. Chiral amine-catalyzed asymmetric Baylis-Hillman reaction: A reliable route to highly enantiomerically enriched (alpha-methylene-beta-hydroxy)esters Peer-reviewed

    Y Iwabuchi, M Nakatani, N Yokoyama, S Hatakeyama

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 121 (43) 10219-10220 1999/11

    DOI: 10.1021/ja992655+  

    ISSN: 0002-7863

  213. Efficient route to functionalized eight-membered lactones based on intramolecular silicon-directed acylative ring-opening reactions of 3-(tetrahydro-2-furyl)propanoic acid derivatives

    H Ohi, S Inoue, Y Iwabuchi, H Irie, S Hatakeyama

    SYNLETT (11) 1757-1759 1999/11

    ISSN: 0936-5214

  214. A modified bait and switch strategy for the generation of esterolytic abzymes using concerted catalytic mechanisms

    Y Iwabuchi, S Kurihara, M Oda, Fujii, I

    TETRAHEDRON LETTERS 40 (29) 5341-5344 1999/07

    DOI: 10.1016/S0040-4039(99)00972-7  

    ISSN: 0040-4039

  215. Buta-2,3-dienylstannanes, effective reagents for regioselective buta-1,3-dienylation of aldehydes and acetals

    MM Luo, Y Iwabuchi, S Hatakeyama

    CHEMICAL COMMUNICATIONS (3) 267-268 1999/02

    DOI: 10.1039/a809081e  

    ISSN: 1359-7345

  216. Regioselective buta-1,3-dienylation of aldehydes via transmetallation of 2-tributylstannylbuta-1,3-diene

    Meiming Luo, Yoshiharu Iwabuchi, Susumi Hatakeyama

    Synlett (7) 1109-1111 1999

    Publisher: Georg Thieme Verlag

    DOI: 10.1055/s-1999-2787  

    ISSN: 0936-5214

  217. New metabolic pathway of (24R)-24,25-dihydroxyvitamin D3: Epimerization of the 3-hydroxy group

    Tatsuya Higashi, Ryuta Kikuchi, Kanako Miura, Kazutake Shimada, Hiroko Hiyamizu, Hidenori Ooi, Yoshiharu Iwabuchi, Susumi Hatakeyama, Noboru Kubodera

    Biological and Pharmaceutical Bulletin 22 (7) 767-769 1999

    Publisher: Pharmaceutical Society of Japan

    DOI: 10.1248/bpb.22.767  

    ISSN: 0918-6158

  218. 118(P58) Synthetic Study of (-)-Dysiherbaine, a New Marine Neurotoxic Amino Acid

    Maeyama Junji, Kamada Kazuko, Iwabuchi Yoshiharu, Hatakeyama Susumi

    Symposium on the Chemistry of Natural Products, symposium papers (40) 697-702 1998/08/31

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.40.0_697  

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    (-)-Dysiherbaine was isolated from a Micronesian sponge Dysidea herbacea after screening for substances that exhibit potent neurotoxic activity. This amino acid was found to be a selective agonist of non-NMDA type glutamate receptors in CNS. The relative structure was determined spectroscopically to be a novel di-amino di-carboxylic acid consisting of a cis fused-hexahydrofuro[3,2-b]pyran ring substituted with a 3-[2-aminopropanoic acid] side chain. However, its absolute structure has not been determined yet. The combination of its unique molecular architecture and potent biological activity prompted us to commence the synthetic investigation on (-)-dysiherbaine. Retrosynthetic analysis of dysiherbaine led to tricyclic lactone 3 as a key intermediate. The strategy we have employed to construct the cis fused-hexahydrofuro[3,2-b]pyran core of 3 relies on the versatility of chiral epoxy alcohol 4 which is available from the Katsuki-Sharpless asymmetric epoxidation of σ-symmetrical divinyl carbinol 5. Thus, tricyclic lactone 3 was synthesized through the following major transformations (i, inversion of the hydroxy group of 4 giving 6; ii, stereo- and regioselective introduction of nitrogen atom giving 11 by the reaction of 6 with benzoyl isocyanate followed by base-treatment; iii, conversion of 11 to butenolide 14 via (Z)-α,β-unsaturated ester 13; iv, BCl_3 promoted debenzylation followed by intramolecular Michael addition of the deprotected hydroxy group to the butenolide ring). We could synthesized an advanced intermediate 19 from 3 via nitrile 2 by a four-step sequence involving DIBAL reduction, acetylation, cyanation, and alkylation of 2 with allyl bromide in the presence of (TMS)_2NNa. Although the stereochemistry of the newly formed C-4 asymmetric center is unknown, the remaining task is the construction of the 2-aminopropanoic acid moiety, for example, by ozonolysis, Strecker reaction, and hydrolysis. Furthermore, another advanced intermediate 22 having 2-amino-2-cyanopropyl side chain was also prepared from 3 by a six step sequence involving formation of Weinreb amide 20, Grignard reaction with allylmagnesium chloride followed by intramolecular ketalization giving 21, ozonolysis, Strecker reaction, and acetylation. Lewis acid catalyzed cyanation of 22 is now under investigation to achieve a total synthesis of dysiherbaine from 22.

  219. Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction

    T Nishioka, Y Iwabuchi, H Irie, S Hatakeyama

    TETRAHEDRON LETTERS 39 (31) 5597-5600 1998/07

    DOI: 10.1016/S0040-4039(98)01130-7  

    ISSN: 0040-4039

  220. Evolving catalytic antibodies in a phage-displayed combinatorial library

    Fujii, I, S Fukuyama, Y Iwabuchi, R Tanimura

    NATURE BIOTECHNOLOGY 16 (5) 463-467 1998/05

    DOI: 10.1038/nbt0598-463  

    ISSN: 1087-0156

  221. Synthesis of viridiofungin A trimethyl ester and determination of the absolute structure of viridiofungin A

    T Esumi, Y Iwabuchi, H Irie, S Hatakeyama

    TETRAHEDRON LETTERS 39 (8) 877-880 1998/02

    DOI: 10.1016/S0040-4039(97)10754-7  

    ISSN: 0040-4039

  222. Preparation of 2-iodo-1,3-butadienes from 1-trimethylsilyl-2,3-butadienes and their functionalizations

    T Nishiyama, T Esumi, Y Iwabuchi, H Irie, S Hatakeyama

    TETRAHEDRON LETTERS 39 (1-2) 43-46 1998/01

    DOI: 10.1016/S0040-4039(97)10413-0  

    ISSN: 0040-4039

  223. A new stereoselective route to (-)-octalactin A based on intramolecular SmI2 promoted Reformatsky reaction

    Susumu Inoue, Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama

    Synlett (7) 735-736 1998

    Publisher: Georg Thieme Verlag

    DOI: 10.1055/s-1998-1778  

    ISSN: 0936-5214

  224. A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes

    S Hatakeyama, M Yoshida, T Esumi, Y Iwabuchi, H Irie, T Kawamoto, H Yamada, M Nishizawa

    TETRAHEDRON LETTERS 38 (45) 7887-7890 1997/11

    DOI: 10.1016/S0040-4039(97)10077-6  

    ISSN: 0040-4039

  225. Synthetic studies of vitamin D analogs .24. Convergent synthesis of 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D-3 (ED-71)

    S Hatakeyama, T Ikeda, J Maeyama, T Esumi, Y Iwabuchi, H Irie, A Kawase, N Kubodera

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 7 (22) 2871-2874 1997/11

    DOI: 10.1016/S0960-894X(97)10095-6  

    ISSN: 0960-894X

  226. Enantioselective preparation of 1-benzyloxy-3-methyl-6-heptene-2,4-diols: Total synthesis of (+)-prelactone C

    T Esumi, H Fukuyama, R Oribe, K Kawazoe, Y Iwabuchi, H Irie, S Hatakeyama

    TETRAHEDRON LETTERS 38 (27) 4823-4826 1997/07

    DOI: 10.1016/S0040-4039(97)01042-3  

    ISSN: 0040-4039

  227. Reaction properties of immobilized catalytic antibodies that deprotect acylated carbohydrates

    A Kondo, H Fukuda, Y Iwabuchi, Fujii, I

    JOURNAL OF FERMENTATION AND BIOENGINEERING 82 (5) 452-457 1996

    DOI: 10.1016/S0922-338X(97)86982-6  

    ISSN: 0922-338X

  228. 26 APPLICATION OF CATALYTIC ANTIBODIES FOR FACILE SYNTHESIS OF OLIGOSACCHARIDES

    IWABUCHI Yoshiharu, SUGIHARA Yoshiaki, FUKUYAMA Shiro, FUJII Ikuo

    Symposium on the Chemistry of Natural Products, symposium papers (37) 150-155 1995/09/01

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.37.0_150  

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    Considering the inherent high binding specificity of antibodies, catalytic antibodies in which the substrate specificity and the reaction pathway can be programmed by the hapten could provide powerful tools for regio- and stereoselective organic synthesis. In particular, regioselective protection and/or deprotection of carbohydrates in oligosaccharide synthesis are interesting targets for testing the potential of catalytic antibodies. Recently, we have reported the generation of catalytic antibody 17E11 which is capable of discriminating between chemically identical functional groups in the same molecule, catalyzing regioselective deprotection of acylated carbohydrates. Examination of the substrate specificity of antibody 17E11 showed the desired specificity as well as the applicability to a wide range of substrates. Thus, antibody 17E11 is capable of recognizing the regio- and stereochemistry at C-3 and C-4, and only the ester group at C-4 is hydrolyzed exclusively in acylated gluco-type carbohydrates possessing a variety of substituents at C-1, C-2, and C-6. To extend catalytic antibody technology for practical use, we have attempted to utilize antibody 17E11 at several steps associated in oligosacchride synthesis. As a result, it has been demonstrated that these catalytic antibodies efficiently hydrolyze a variety of carbohydrate esters and resulting 4-OH products can be used as glycosyl acceptors in syntheses of oligosaccharide and glycopeptide. The potentiality of the antibody-catalyst for synthesis of some oligosaccharides will be discussed.

  229. Catalytic antibody and its medical applications

    I. Fujii, Y. Iwabuchi

    Nippon rinsho. Japanese journal of clinical medicine 53 518-527 1995/02/01

    ISSN: 0047-1852

  230. REGIOSELECTIVE AND STEREOSELECTIVE DEPROTECTION OF ACYLATED CARBOHYDRATES VIA CATALYTIC ANTIBODIES

    Y IWABUCHI, H MIYASHITA, R TANIMURA, K KINOSHITA, M KIKUCHI, FUJII, I

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 116 (2) 771-772 1994/01

    DOI: 10.1021/ja00081a049  

    ISSN: 0002-7863

  231. 26 Regio- and Stereoselective Hydrolysis of Ester Bond on Carbohydrate by Catalytic Antibody

    Iwabuchi Y., Karaki Y., Miyashita H., Kinoshita K., Hara T., Tanimura R., Kikuchi M., Fujii I.

    Symposium on the Chemistry of Natural Products, symposium papers (35) 194-201 1993/09/10

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.35.0_194  

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    In the field of carbohydrate chemistry, differentiation of the potentially competing functions is rather formidable. For example, the extension of an oligosaccharide at a single glucose entity requires the identification of one of five hydroxyls to function as glycosyl acceptor. Chemists carry out multi-step protection-deprotection processes by the combination of many protective groups, such as esters, ethers, carbonates, ketals etc., to resolve this problem. Generation of a catalytic antibody which recognizes and catalyzes the hydrolysis of certain ester bond as programmed by the hapten might simplify oligosacchride synthesis. We designed and synthesized hapten-KLH conjugate 5 to generate monoclonal antibodies that catalyze selective hydrolysis of the 4-positioned ester of glucose derivatives. The immunization elicited fourteen IgG which bound to the hapten portion. Two IgG were found to catalyze the hydrolysis reaction of the substrate 17 at the directed 4-position selectively with significant rate enhancement compared to the uncatalyzed background reaction. One antibody (17E11) was further characterized in detail.

  232. TOTAL SYNTHESIS OF CALICHEAMICIN-GAMMA-1(I) .1. SYNTHESIS OF THE OLIGOSACCHARIDE FRAGMENT

    RD GRONEBERG, T MIYAZAKI, NA STYLIANIDES, TJ SCHULZE, W STAHL, EP SCHREINER, T SUZUKI, Y IWABUCHI, AL SMITH, KC NICOLAOU

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 115 (17) 7593-7611 1993/08

    DOI: 10.1021/ja00070a004  

    ISSN: 0002-7863

  233. X-Neu5Ac: A novel substrate for chromogenic assay of neuraminidase activity in bacterial expression systems

    Ikuo Fujii, Yoshiharu Iwabuchi, Tadashi Teshima, Tetsuo Shiba, Masakazu Kikuchi

    Bioorganic and Medicinal Chemistry 1 (2) 147-149 1993

    DOI: 10.1016/S0968-0896(00)82112-4  

    ISSN: 0968-0896

  234. TOTAL SYNTHESIS OF SIALYL DIMERIC LEX

    KC NICOLAOU, CW HUMMEL, Y IWABUCHI

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 114 (8) 3126-3128 1992/04

    DOI: 10.1021/ja00034a063  

    ISSN: 0002-7863

  235. Total Synthesis of Calicheamicin–Dynemicin Hybrid Molecules

    K. C. Nicolaou, Erwin P. Schreiner, Yoshiharu Iwabuchi, Toshio Suzuki

    Angewandte Chemie International Edition in English 31 340-342 1992/01/01

    DOI: 10.1002/anie.199203401  

    ISSN: 0570-0833

  236. 13 THE KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION OF ALKENYLETHYLENE GLYCOL AND ITS UTILIZATION FOR THE NATURAL PRODUCT SYNTHESIS

    Takano S., Iwabuchi Y., Yoshimitsu T., Ogasawara K.

    Symposium on the Chemistry of Natural Products, symposium papers (33) 94-100 1991/09/07

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.33.0_94  

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    Unprecedented high enantiospecific epoxidation of alkenylethylene glycol substrates under the Katsuki-Sharpless asymmetric conditions has been first recognized. Both dissymmetric and symmetric (C_2 and Cs) substrates underwent facile epoxidation in highly enantio- and diastereo-specific manners with inversed selection modes established in the conventional allylic alcohol substrates. Thus, dissymmetric and C_2-symmetric substrates afforded the corresponding epoxides in inversed enantio- and diastereo-selection modes, while C_2 (meso)-symmetric substrate afforded the epoxide in inversed enantioselection mode. Moreover, complete enantio- and diastereo-selective discrimination of two chemically equivalent vinyl groups in 2,2-bis-vinylethylene glycol substrate has also been observed under the epoxidation conditions. The observed stereochemical outcome, especially, that observed with the C_2 (meso) and the 2,2-bis-divinyl substrates, seemed to support that the monomer mechanism rather than the dimer mechanism is involved in the reaction of the 2-alkenyl-1,2-ethyleneglycol substrates. As a practical application of the present finding, a new enantiocontrolled synthesis of L-erythro- and D-threo-sphingosines has been established using the epoxides obtained from the C_2- and the Cs-symmetric substrates, respectively.

  237. INVERSION OF DIASTEREOFACIAL AND ENANTIOFACIAL SELECTIVITIES IN THE KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION OF (E)-ALKENYLETHYLENE GLYCOLS

    S TAKANO, Y IWABUCHI, K OGASAWARA

    SYNLETT 1991 (8) 548-550 1991/08

    DOI: 10.1055/s-1991-20791  

    ISSN: 0936-5214

  238. THE KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION OF (E)-2,5-DIHYDROXY-2,5-DIMETHYL-3-HEXENE

    S TAKANO, Y IWABUCHI, K OGASAWARA

    TETRAHEDRON LETTERS 32 (29) 3527-3528 1991/07

    DOI: 10.1016/0040-4039(91)80823-O  

    ISSN: 0040-4039

  239. INVERSION OF ENANTIOSELECTIVITY IN THE KINETIC RESOLUTION MODE OF THE KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION REACTION

    Yoshiharu Iwabuchi

    Journal of the American Chemical Society 113 2786-2787 1991/01/01

    DOI: 10.1021/JA00007A082  

    ISSN: 0002-7863

  240. An enantio- and stereo-controlled synthesis of L-erythro- and D-threo-C18-sphingosines via the anomalous version of the katsuki-sharpless asymmetric epoxidation reaction

    Seiichi Takano, Yoshiharu Iwabuchi, Kunio Ogasawara

    Journal of the Chemical Society, Chemical Communications (12) 820-821 1991

    DOI: 10.1039/C39910000820  

    ISSN: 0022-4936

  241. 43 ENANTIOCONTROLLED ROUTE TO SOME ISOPRENOID NATURAL PRODUCTS BY NEW CHIRAL α-ACETYLENE ALCOHOL SYNTHESIS

    Takano S., Iwabuchi Y., Sugihara T., Samizu K., Shimazaki Y., Ogasawara K.

    Symposium on the Chemistry of Natural Products, symposium papers (32) 320-327 1990/09/25

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.32.0_320  

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    An efficient general method for the construction of chiral α-acetylene alcohols has been developed. The new method consists of the Katsuki-Sharpless asymmetric epoxidation of allylic alcohol substrates, conversion of the chiral epoxides into the corresponding chloro-epoxides, and brief exposure of the latter products with an excess n-butyllithium in tetrahydrofuran. The reaction leads to the formation of the corresponding terminal α-acetylene alcohols readily in excellent yields without affecting original chiral integrities introduced in the asymmetric epoxidation reaction. Employing the new chiral α-acetylene alcohol formation reaction as the key step as well as using a chiral acetylene alcohol thus generated as a common building block, some isoprenoid natural products ranging from mevalonolactone to α-tocopherol have been synthesized in an enantiocontrolled sequence of reactions. Namely, a single acetylene alcohol obtained has been sequentially elongated via a monoterpenoid citronellal, a sesquiterpenoid perhydrofarnesol, and a diterpenoid phytol by iterative application of the key reaction to complete a linear synthesis of α-tocopherol. On the other hand, the same acetylene alcohol has been separately transformed into the two known segments, chromanethanol and the perhydronor-farnesol, to complete a convergent synthesis of α-tocopherol. During these transformations, an isoprenoid biogenetic precursor mevalonolactone, olfactive monoterpenoids, linalool, cis- and trans-rose oxides, and an irregular phenolic monoterpenoid bakuchiol have been synthesized from the same acetylene alcohol in enantiocontrolled ways.

  242. PRACTICAL ROUTE TO BOTH (S)-ENANTIOMER AND (R)-ENANTIOMER OF O-(4-METHOXYPHENYL)GLYCIDOL USING (S)-1,2-O-ISOPROPYLIDENEGLYCEROL AS A COMMON PRECURSOR

    S TAKANO, M MORIYA, M SUZUKI, Y IWABUCHI, T SUGIHARA, K OGASAWARA

    HETEROCYCLES 31 (8) 1555-1563 1990/08

    DOI: 10.3987/COM-90-5476  

    ISSN: 0385-5414

  243. A CHIRAL ROUTE TO BOTH ENANTIOMERS OF PHYSOSTIGMINE AND THE 1ST SYNTHESIS OF (-)-NORPHYSOSTIGMINE Peer-reviewed

    S TAKANO, M MORIYA, Y IWABUCHI, K OGASAWARA

    CHEMISTRY LETTERS (1) 109-112 1990/01

    ISSN: 0366-7022

    eISSN: 1348-0715

  244. A CONVERGENT ENANTIOCONTROLLED ROUTE TO MEVALONOLACTONE AND VITAMIN-E FROM (S)-O-BENZYLGLYCIDOL

    S TAKANO, Y SHIMAZAKI, Y IWABUCHI, K OGASAWARA

    TETRAHEDRON LETTERS 31 (25) 3619-3622 1990

    DOI: 10.1016/S0040-4039(00)94459-9  

    ISSN: 0040-4039

  245. AN ENANTIOCONVERGENT ROUTE TO (-)-ANISOMYCIN FROM BOTH (S)-ENANTIOMERS AND (R)-ENANTIOMERS OF EPICHLOROHYDRIN

    S TAKANO, Y IWABUCHI, K OGASAWARA

    HETEROCYCLES 29 (10) 1861-1864 1989/10

    DOI: 10.3987/COM-89-5104  

    ISSN: 0385-5414

  246. 16 ENANTIOCONTROLLED SYNTHESIS OF NATURAL PRODUCTS UTILIZING BICYCLO[2.2.1]HEPTANE SYNTHONS

    Takano S., Inomata K., Sato T., Samizu K., Sugihara T., Iwabuchi Y., Takahashi M., Ogasawara K.

    Symposium on the Chemistry of Natural Products, symposium papers (31) 112-119 1989/09/17

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.31.0_112  

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    Some potentially useful chiral building blocks bearing bicyclo[2.2.1]heptane framework utilizable enantiodivergently have been prepared in optically pure forms from D-mannitol by chemically and from dicyclopentadiene by enzymatically. Owing to their rigid framework and high functionality, chemical transformations could be carried out efficiently in highly stereo-controlled manners. Moreover, their latent symmetric structures allowed enantiodivergent synthesis of the target molecules. Potentiality of the chiral synthons thus prepared has been demonstrated by establishing enantiocontrolled routes to the following compounds: α-yohimbane indole alkaloids, (-)-nitraraine, (-)-dihydronitraraine, a key prostaglandin intermediate, (4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-2-cyclopenten-1-one, sandal oil sesquiterpenes, (+)- and (-)-β-santalene, (+)- and (-)-epi-β-santalene, a cuparene type sesquiterpene, (+)- and ()-α-cuparenone, the first simple benzomorphane type alkaloid, (+)- and (-)-aphanorphine, and a calabar bean alkaloid, (+)- and (-)-physostigmine. The present synthesis did not support the proposed structures for nitraraine and dihydronitraraine. Proposed relative structure of (-)-aphanorphine was first confirmed by the present synthesis which also established the absolute structure of the first simple benzomorphane natural product which remained undetermined.

  247. A CONCISE ENANTIOSELECTIVE SYNTHESIS OF ACROMELIC ACID-B FROM (S)-O-BENZYLGLYCIDOL

    S TAKANO, S TOMITA, Y IWABUCHI, K OGASAWARA

    HETEROCYCLES 29 (8) 1473-1476 1989/08

    DOI: 10.3987/COM-89-5064  

    ISSN: 0385-5414

  248. A CONVENIENT ONE-FLASK SYNTHESIS OF ALPHA-METHYLENEALDEHYDES FROM PRIMARY ALCOHOLS Peer-reviewed

    S TAKANO, K INOMATA, K SAMIZU, S TOMITA, M YANASE, M SUZUKI, Y IWABUCHI, T SUGIHARA, K OGASAWARA

    CHEMISTRY LETTERS (7) 1283-1284 1989/07

    ISSN: 0366-7022

    eISSN: 1348-0715

  249. A concise enantioselective synthesis of (+)-muscarine from (R)-O-benzylglycidol [(R)-benzyloxymethyloxirane]

    Seiichi Takano, Yoshiharu Iwabuchi, Kunio Ogasawara

    Journal of the Chemical Society, Chemical Communications (18) 1371-1372 1989

    DOI: 10.1039/C39890001371  

    ISSN: 0022-4936

  250. CONCISE SYNTHESIS OF C-2-SYMMETRIC TRANS-2,5-DIOXYMETHYLPYRROLIDINE DERIVATIVES BY NOVEL CYCLIZATION

    S TAKANO, M MORIYA, Y IWABUCHI, K OGASAWARA

    TETRAHEDRON LETTERS 30 (29) 3805-3806 1989

    DOI: 10.1016/S0040-4039(01)80661-4  

    ISSN: 0040-4039

  251. CONCISE STEREOSELECTIVE SYNTHESIS OF (2S,4R)-4-HYDROXYPROLINE FROM (S)-O-BENZYLGLYCIDOL BY A NOVEL CYCLIZATION

    S TAKANO, Y IWABUCHI, K OGASAWARA

    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS (23) 1527-1528 1988/12

    DOI: 10.1039/C39880001527  

    ISSN: 0022-4936

  252. CONFIGURATIONAL CORRELATIONS OF SOME SECONDARY ALCOHOLS BY H-1-NMR SPECTROSCOPY

    Yoshiharu Iwabuchi

    Chemistry Letters 1988

    DOI: 10.1246/CL.1988.1827  

  253. A concise enantioselective route to (-)-kainic acid from (S)-2-(benzyloxymethyl)oxirane

    Seiichi Takano, Yoshiharu Iwabuchi, Kunio Ogasawara

    Journal of the Chemical Society, Chemical Communications (17) 1204-1206 1988

    DOI: 10.1039/C39880001204  

    ISSN: 0022-4936

  254. A CONCISE ENANTIOSELECTIVE SYNTHESIS OF ACROMELIC ACID-A

    S TAKANO, Y IWABUCHI, K OGASAWARA

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 109 (18) 5523-5524 1987/09

    DOI: 10.1021/ja00252a037  

    ISSN: 0002-7863

  255. 11 CHIRAL ROUTES TO THE KAINOID AMINO ACIDS

    Takano Seiichi, Sugihara Takumichi, Iwabuchi Yoshiharu, Satoh Shigeki, Ogasawara Kunio

    Symposium on the Chemistry of Natural Products, symposium papers (29) 79-86 1987/07/25

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.29.0_79  

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    Two potentially useful enantioselective routes to the kainoid amino acids have been developed based on two intramolecular pericyclic reactions using diethyl (L)-tartrate and (S)-O-benzylglycidol as chiral starting materials, respectively. Reaction of the δ,ε-unsaturated aldehyde 29c, prepared from diethyl (L)-tartrate, with Meldrum's acid 7 afforded a single adduct 31b diastereoselectively via spontaneous condensation and intramolecular hetero-Diels-Alder reaction. Hydrolysis of 31b gave the bicyclic lactone 32b bearing newly generated three contiguous chiral centers on the pyrrolidine ring whose structure was confirmed by converting it into kainic acid lactone 33, the known compound generated from kainic acid 1 by acid treatment. Reduction of 32b, followed by regioselective dehydration of the product 34 yielded the potential intermediate 35 of kainic acid 1. On the other hand, thermolysis of both alkyl-44a and aryl-44b-cis-olefinic aziridine esters, 44a and 44b, prepared from (S)-O-benzylglycidol 40, yielded the corresponding all-cis-trisubstituted pyrrolidines, 45a and 45b, diastereoselectively, via spontaneous generation of the 1,3-dipoles, 43a and 43b, and their intra-molecular [1,3]-dipolar cyclization. The former adduct 45a was converted into the potential intermediate 50 of kainic acid 1 via the α,β-unsaturated aldehyde 48. The latter adduct 45b was successfully transformed into acromelic acid A 4, toxic principle of the poisonous mushroom Clitocybe acromelalga, via highly stereoselective epimerization of the all-cis-diester 54.

  256. A Convenient Synthesis of 2-Cyclopentenone

    Seiichi Takano, Yoshiharu Iwabuchi, Michiyasu Takahashi, Kunio Ogasawara

    Chemical and Pharmaceutical Bulletin 34 (8) 3445-3446 1986

    DOI: 10.1248/cpb.34.3445  

    ISSN: 1347-5223 0009-2363

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  3. THE UTILITY OF OXOAMMONIUM SPECIES IN ORGANIC SYNTHESIS: BEYOND ALCOHOL OXIDATION

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    Heterocycles 105 (1) 61-114 2022

    DOI: 10.3987/REV-21-SR(R)2  

    ISSN: 0385-5414

    eISSN: 1881-0942

  4. Directing carboxylic acid dehydrogenation

    Yoshiharu Iwabuchi

    Science 374 (6572) 1199-1199 2021/12/03

    DOI: 10.1126/science.abm4457  

    ISSN: 0036-8075

    eISSN: 1095-9203

  5. Studies directed toward the creation of induced pluripotent small (iPS) molecules based on naturally occurring polyene macrolactams

    叶直樹, 叶直樹, 寺嶋優太, 田中卓, 寺島隆世, 西山大陸, 長澤翔太, 笹野裕介, 岩渕好治

    複素環化学討論会講演要旨集 50th 2021

  6. アンサマクロラクタム抗腫瘍活性天然物Cytotrienin Aの合成研究

    建石悠貴, 佐藤亮, 小松慎吾, 野口正嗣, 長澤翔太, 笹野裕介, 叶直樹, 岩渕好治

    創薬懇話会講演要旨集 2021 2021

  7. Studies aimed at the synthesis and mode of action of heronamide C analogues

    西山大陸, 寺島隆世, 長澤翔太, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(Web) 141st 2021

    ISSN: 0918-9823

  8. Synthetic study of the marine alkaloid chartelline C benzene analog

    永山晶子, 黒田麻由, 上杉惇一郎, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(Web) 141st 2021

    ISSN: 0918-9823

  9. Synthetic Study of Cytotrienin A (2)

    建石悠貴, 佐藤亮, 小松慎吾, 野口正嗣, 長澤翔太, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(Web) 141st 2021

    ISSN: 0918-9823

  10. Aerobic oxidation of primary alcohols with nitroxyl radical/copper catalysis and one-pot reaction consisting of the alcohol oxidation and Z-selective HWE Reaction

    山一蒼仁, 笹野裕介, 田中卓, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 140th (Web) 2020

  11. Preparation of Novel Fluorinated Compounds by Using Newly Developed gem-Difluoropropargyl Ether Synthesis

    岡村俊孝, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 140th (Web) 2020

  12. Synthetic Study on Himalensines

    小山純平, 笹野裕介, 叶直樹, 岩渕好治

    万有仙台シンポジウム 31st 2020

  13. ジフルオロプロパルギルエノールエーテル合成法の開発と応用

    岡村俊孝, 小山田健太, 金澤純一郎, 宮本和範, 内山真伸, 岩渕好治, 叶直樹

    日本薬学会関東支部大会講演要旨集 64th 2020

  14. 海洋性アルカロイドchartelline Cベンゼンアナログの合成研究

    永山晶子, 黒田麻由, 上杉惇一郎, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 59th 2020

  15. Synthetic Study of Cytotrienin A

    建石悠貴, 佐藤亮, 小松慎吾, 長澤翔太, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 140th (Web) 2020

  16. Actinomyces derived polyene macrolactam. Synthetic study on sceliphrolactam putative structure (2).

    小山栞, 真野昂裕, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 140th (Web) 2020

  17. ジフルオロプロパルギルブロミドを利用したニコラス型新規分子変換反応の開発と応用

    岡村俊孝, 岩渕好治, 叶直樹

    次世代を担う有機化学シンポジウム講演要旨集 17th 2019

  18. ニトロキシルラジカル/銅触媒的な化学選択的アルコール空気酸化-HWE反応によるα,β-不飽和エステルの擬ワンポット合成

    笹野裕介, 山一蒼仁, 田中卓, 叶直樹, 岩渕好治

    有機合成シンポジウム講演要旨集 115th 2019

  19. 高度縮合多環式ユズリハアルカロイド・カリシフィリンAの合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    創薬懇話会講演要旨集 2019 2019

  20. 生物活性分子へのプロパルギル単位導入反応の開発とその応用

    藤木翔吾, 岡村俊孝, 岩渕好治, 叶直樹, 叶直樹

    創薬懇話会講演要旨集 2019 2019

  21. ジフルオロプロパルギルブロミドを用いた新規Nicholas型分子変換反応の開発と応用

    岡村俊孝, 岩渕好治, 叶直樹

    万有仙台シンポジウム 30th 2019

  22. ニトロキシルラジカル/銅触媒を用いたアルコール空気酸化-HWE反応によるα,β-不飽和エステルの擬ワンポット合成

    山一蒼仁, 笹野裕介, 田中卓, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 139th 2019

  23. 新規ジフルオロプロパルギルエノールエーテル形成法の開発と応用

    岡村俊孝, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 139th 2019

  24. 放線菌由来ポリエンマクロラクタムSceliphrolactam推定構造の合成研究

    小山栞, 真野昂裕, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 139th 2019

  25. 芳香族生物活性分子への触媒的プロパルギル単位導入反応の開発(2)

    藤木翔吾, 岡村俊孝, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 139th 2019

  26. 作用機序解析を志向したheronamide C類縁体の合成研究

    西山大陸, 寺島隆世, 岩渕好治, 叶直樹

    日本薬学会東北支部大会講演要旨集 58th 2019

  27. Cytotrienin Aの合成研究:鈴木カップリングによるトリエン単位構築の検討

    建石悠貴, 佐藤亮, 小松慎吾, 野口正嗣, 長澤翔太, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 58th 2019

  28. ニコラス型反応を用いた新規α-フルオロエーテル合成法の開発

    岡村俊孝, 岡村俊孝, 岩渕好治, 叶直樹

    日本薬学会関東支部大会講演要旨集 63rd 2019

  29. Synthetic Studies on (+)-Cytotrienin A, an Apoptosis Inducing Ansamycin Antibiotic

    岩渕好治, 佐藤亮, 笹野裕介, 小松慎吾, 野口正嗣, 掛谷秀昭, 長田裕之, 叶直樹

    天然有機化合物討論会講演要旨集(Web) 60th 2018

    ISSN: 2433-1856

  30. 放線菌由来ポリエンマクロラクタム8-デオキシヘロナミドCの収束的全合成

    寺島隆世, 寺嶋優太, 田中卓, 岩渕好治, 叶直樹

    複素環化学討論会講演要旨集 48th 2018

  31. 抗腫瘍活性ユズリハアルカロイドDaphnicyclidin AのBCD環部の立体選択的合成

    岡本健寛, 笹野裕介, 川住宗生, 宮城琢, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 138th 2018

  32. 芳香族生物活性分子の触媒的プロパルギル化反応の開発

    藤木翔吾, 岡村俊孝, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 138th 2018

  33. 作用機序解析への応用を指向した生物活性分子の新規ジフルオロプロパルギル化法の開発

    岡村俊孝, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 138th 2018

  34. ニトロキシルラジカル/銅触媒を用いたアルコール空気酸化-HWE反応によるα,β-不飽和エステルの擬ワンポット合成

    山一蒼仁, 笹野裕介, 田中卓, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 57th 2018

  35. 高度縮合多環式ユズリハアルカロイドカリシフィリンAの合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    反応と合成の進歩シンポジウム講演要旨集 44th 2018

    ISSN: 0919-2123

  36. 金属カルベノイドの官能基選択的挿入反応:アルコールとフェノール間での選択性制御

    李智成, 村上弘晃, 岩渕好治, 叶直樹

    日本薬学会東北支部大会講演要旨集 57th 2018

  37. Sceliphrolactam推定構造の合成研究

    小山栞, 眞野昂裕, 岩渕好治, 叶直樹

    日本薬学会東北支部大会講演要旨集 57th 2018

  38. 新規合成クルクミン誘導体における抗癌剤耐性ABCトランスポーターの抑制効果

    村上 恵, 大沼 忍, 工藤 克昌, 石田 晶玄, 岩渕 好治, 柴田 浩行, 林 洋毅, 元井 冬彦, 内藤 剛, 海野 倫明

    日本癌学会総会記事 76回 J-1014 2017/09

    Publisher: 日本癌学会

    ISSN: 0546-0476

  39. マクロライド系抗生物質FD-891の生合成におけるシトクロムP450酸化酵素GfsFの基質特異性

    高柳龍一, 古谷隆, 宮永顕正, 工藤史貴, 江口正, 川又綾乃, 岩渕好治, 叶直樹

    日本化学会春季年会講演予稿集(CD-ROM) 97th 2017

  40. 脂肪族およびフェノール性水酸基に対する金属カルベノイドの官能基選択的挿入反応の開発

    村上弘晃, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 137th 2017

  41. 新規P450基質スクリーニング法を用いたP450BM3変異体の基質特異性解析

    川又綾乃, 鈴木花奈, 高橋裕介, 守谷崇, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 137th 2017

  42. 抗腫瘍活性C5-curcuminoidのプロドラッグ化を指向したチオール付加体の合成と構造活性相関研究

    福田宙央, 高山亜紀, 山越博幸, 叶直樹, 柴田浩行, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 137th 2017

  43. 芳香族生物活性小分子に対する直接的アルキン化法の開発

    岡村俊孝, 鈴木貴大, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 137th 2017

  44. ランタニドトリフラートを触媒としたエポキシアルコールの位置選択的開環反応の最適化

    中村大地, 笹野裕介, 上杉惇一郎, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 137th 2017

  45. 放線菌由来ポリエンマクロラクタム8-deoxyheronamide Cの全合成研究

    寺嶋優太, 田中卓, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 137th 2017

  46. 放線菌由来ポリエンマクロラクタムniizalactam Cの合成研究

    真野昂裕, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 137th 2017

  47. 抗腫瘍活性ユズリハアルカロイドDaphniyunnine Dの合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 137th 2017

  48. Thymic stromal lymphopoietin産生抑制化合物の抗アレルギー作用とその標的タンパク質の探索

    須藤栞, 瀬川良佑, 白木美香, 岡村俊孝, 叶直樹, 岩渕好治, 平澤典保

    日本薬学会東北支部大会講演要旨集 56th 2017

  49. ランタノイドトリフラートを触媒とする3,4-エポキシアルコールの位置選択的アミノリシス反応の開発と応用

    松井将吾, 笹野裕介, 上杉惇一郎, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 56th 2017

  50. 置換アルキンに対する位置選択的ヒドロホウ素化のポリエン天然物合成への応用

    寺島隆世, 田中卓, 真野昂裕, 岩渕好治, 叶直樹

    日本薬学会東北支部大会講演要旨集 56th 2017

  51. α-メチレン-γ-ブチロラクトンの効率的合成法の開発とセスキテルペノイド天然物の合成研究

    川口里紗, 福田宙央, 山口千歳, 長澤翔太, 濱直人, 叶直樹, 岩渕好治

    複素環化学討論会講演要旨集 47th 2017

  52. 抗腫瘍活性ユズリハアルカロイド・ダフニユニン類の合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    メディシナルケミストリーシンポジウム講演要旨集 35th 2017

    ISSN: 0919-214X

  53. ビシクロ[5.3.0]デカン型キラル合成素子の開発と天然物合成への応用

    森崎敬介, 小関尊弘, 澁田拓郎, 濱直人, 笹野裕介, 叶直樹, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム 27th 2016

  54. がん細胞遊走阻害活性天然物fusarisetin Aの合成研究

    高山亜紀, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 136th 2016

  55. 抗腫瘍性マクロライドFD-891及びその類縁体合成と構造活性相関研究

    板垣友宏, 川又綾乃, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 136th 2016

  56. (-)-Fumimycinの全合成研究

    西田佳祐, 澁田拓郎, 小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 136th 2016

  57. NAD(P)+検出プローブを利用したP450基質スクリーニング系の改良と評価

    高橋裕介, 守谷崇, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 136th 2016

  58. N-保護2,3-アジリジノアルコールの位置選択的開環反応の開発

    上杉惇一郎, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 136th 2016

  59. Heronamide Cを模倣した多能性ポリエン骨格の迅速合成研究

    田中卓, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 55th 2016

  60. Daphniyunnine Dの合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 55th 2016

  61. 発蛍光性ジアゾクマリン化合物を用いた官能基選択的小分子修飾法の開発

    村上弘晃, 岩渕好治, 叶直樹

    日本薬学会東北支部大会講演要旨集 55th 2016

  62. Turkiyenineの全合成研究(2)

    小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 136th 2016

  63. Turkiyenineの全合成研究

    小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 135th 2015

  64. 生合成仮説に基づくtripartilactamの全合成研究

    真野昂裕, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 135th 2015

  65. 光開裂性光親和型アフィニティー樹脂による固定化小分子の定量解析

    鈴木貴大, 岡村俊孝, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 135th 2015

  66. Eu(OTf)3/DTBMP触媒系を用いる2,3-エポキシアルコールの位置選択的開環反応の開発と応用

    上杉惇一郎, 渡辺翼, 今泉貴充, 澁谷正俊, 叶直樹, 岩渕好治

    次世代を担う有機化学シンポジウム講演要旨集 13th 2015

  67. Turkiyenine提唱構造の全合成

    小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム 26th 2015

  68. Eu(OTf)3/DTBMP触媒系を用いる2,3-エポキシアルコールの位置選択的開環反応の開発

    上杉惇一郎, 渡辺翼, 今泉貴充, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 135th 2015

  69. Turkiyenine提唱構造の全合成

    小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    複素環化学討論会講演要旨集 45th 2015

  70. Eu(OTf)3/DTBMP触媒系を用いる2,3-エポキシアルコールの位置選択的開環反応の開発と応用

    上杉惇一郎, 渡辺翼, 今泉貴充, 澁谷正俊, 叶直樹, 岩渕好治

    有機合成シンポジウム講演要旨集 108th 2015

  71. 抗腫瘍活性天然物Arglabinの合成研究

    福田宙央, 濱直人, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 54th 2015

  72. 8-Deoxyheronamide Cの全合成研究

    寺嶋優太, 伊東俊哉, 坂西航平, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 54th 2015

  73. 芳香族生物活性小分子に対する多点同時修飾法の開発

    岡村俊孝, 鈴木貴大, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 54th 2015

  74. がん細胞転移阻害活性天然物(+)-fusarisetin Aの全合成研究

    高山亜紀, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 54th 2015

  75. Heronamide Cの全合成研究(3)-改訂構造の合成と実証-

    伊東俊哉, 坂西航平, 寺嶋優太, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 135th 2015

  76. Heronamides A-Cの全合成と構造改訂,および構造活性相関

    叶直樹, 伊東俊哉, 寺嶋優太, 坂西航平, 岩渕好治, 藤田航平, 杉山龍介, 西村慎一, 掛谷秀昭

    天然有機化合物討論会講演要旨集(Web) 57th 2015

    ISSN: 2433-1856

  77. AZADO Oxidation : The Practical Method for Catalytic Alcohol Oxidation

    43 (6) 41-48 2014/06

    Publisher: シーエムシー出版

    ISSN: 0913-6150

  78. Daphniyunnine類の合成研究

    井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 134th 2014

  79. NAD(P)+選択的検出プローブを利用したチトクロムP450基質スクリーニング法の構築と評価

    守谷崇, 川又綾乃, 高橋裕介, 岩渕好治, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 134th 2014

  80. 新規ヒドロアズレン型キラル合成素子の開発とセスキテルペノイド合成への応用

    小林久剛, 市川龍之介, 小関尊弘, 笹野裕介, 叶直樹, 岩渕好治

    シンポジウム「モレキュラー・キラリティー」講演要旨集 2014 2014

    ISSN: 1881-0861

  81. Daphnicyclidin/Daphniyunnine類の全合成研究

    井口かおり, 笹野裕介, 池田周平, 望月綾香, 澁谷正俊, 叶直樹, 岩渕好治

    複素環化学討論会講演要旨集 44th 2014

  82. 抗腫瘍性マクロライドFD-891およびFD-892の系統的合成研究(2)マクロラクトン部の構築

    板垣友宏, 川又綾乃, 宮崎雄太, 八幡健三, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 134th 2014

  83. 光親和型小分子固定化アフィニティー樹脂の反応性解析

    鈴木貴大, 岡村俊孝, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 53rd 2014

  84. NAD(P)+検出プローブとH2O2検出プローブを併用したP450基質スクリーニング法の開発と応用

    高橋裕介, 守谷崇, 川又綾乃, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 53rd 2014

  85. HeLa細胞に対するhirsutanol類の作用機構の解析

    土井督史, 三橋進也, 川村猛, 児玉龍彦, 鈴木貴大, 叶直樹, 岩渕好治, 生方信

    日本農芸化学会北海道支部講演会講演要旨 2014 2014

  86. Hirsutanol類の作用機構の解析

    土井督史, 三橋進也, 川村猛, 児玉龍彦, 鈴木貴大, 叶直樹, 岩渕好治, 生方信

    日本木材学会北海道支部講演集(Web) (46) 2014

  87. 不飽和ポリケチドマクロラクタムheronamide類の全合成研究

    伊東俊哉, 坂西航平, 寺嶋優太, 叶直樹, 岩渕好治

    天然有機化合物討論会講演要旨集(Web) 56th 2014

    ISSN: 2433-1856

  88. 新規クルクミン類縁体を用いた血管新生抑制効果の検討(Anti-angiogenic potential of newly synthesized curcumin analog)

    杉山 俊輔, 吉野 優樹, 田中 正光, 栗山 正, 岩渕 好治, 石岡 千加史, 柴田 浩行

    日本癌学会総会記事 72回 315-315 2013/10

    Publisher: 日本癌学会

    ISSN: 0546-0476

  89. 新規C-5 curcuminoidチオール付加体の合成と抗腫瘍活性評価

    高山 亜紀, 杉山 俊輔, 山越 博幸, 叶 直樹, 角道 祐一, 石岡 千加史, 柴田 浩行, 岩渕 好治

    日本薬学会年会要旨集 133年会 (2) 202-202 2013/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  90. 抗腫瘍活性食用植物成分curcuminをリードとする創薬化学研究

    高山亜紀, 山越博幸, 叶直樹, 柴田浩行, 岩渕好治

    次世代を担う有機化学シンポジウム講演要旨集 11th 2013

  91. 抗腫瘍性マクロライドFD-891およびFD-892の系統的合成研究

    川又綾乃, 宮崎雄太, 八幡健三, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 133rd 2013

  92. 新規PI(3,5)P2誘導体の合成とvicenistatinの作用機構解析への応用

    真野昂裕, 岩渕好治, 臼井健郎, 叶直樹

    日本薬学会年会要旨集(CD-ROM) 133rd 2013

  93. 2,7-ナフチリジノン型蛍光色素の開発とシトクロムP450基質スクリーニングへの応用

    守谷崇, 川又綾乃, 高橋裕介, 岩渕好治, 叶直樹

    複素環化学討論会講演要旨集 43rd 2013

  94. Daphniyunnine Dの合成研究

    井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 52nd 2013

  95. NAD+選択的プローブを用いてチトクロムP450の基質を網羅的に検出する

    守谷崇, 川又綾乃, 叶直樹, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム 24th 2013

  96. ヒドロアズレノイド型キラル合成素子の開発とEnglerin Aの合成研究への応用

    小関尊弘, 澁田拓郎, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 52nd 2013

  97. Heronamide Cの合成研究(2)

    伊東俊哉, 坂西航平, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM) 133rd 2013

  98. Vicenistatinの作用機構解明を目的としたPI(3,5)P2誘導体の合成

    真野昂裕, 大野裕太郎, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 52nd 2013

  99. 炎症性サイトカインによるシグナル伝達と遺伝子発現に対するirciniastatin Aの作用の解析

    平野誠也, 山田有里子, 渡辺翼, 叶直樹, 岩渕好治, 臼井健郎, 片岡孝夫

    日本分子生物学会年会プログラム・要旨集(Web) 36th 2013

  100. 液胞化誘導活性および抗腫瘍活性を有する天然物Vicenistatinの構造活性相関研究

    ONO YUTARO, FUKUDA HAYATO, NISHIYAMA YUKO, NAKAMURA RIENA, IWABUCHI YOSHIHARU, USUI TAKEO, KANO NAOKI

    日本薬学会年会要旨集(CD-ROM) 133rd (2) ROMBUNNO.28AMA-077-147 2013

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  101. 三置換ビニルヨージドとβ置換ビニルスズ化合物の異常Stilleカップリング反応

    大野裕太郎, 福田隼, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 132nd (2) 184 2012/03/05

    ISSN: 0918-9823

  102. 抗腫瘍性ビオチン化C5-クルクミノイドGO-Y086は細胞内でKSRP/FUBP2に結合する

    山越 博幸, 叶 直樹, 高山 亜紀, 工藤 千枝子, 佐藤 温子, 上田 和則, 室井 誠, 昆 俊亮, 佐竹 正延, 大堀 久詔, 石岡 千加史, 大島 吉輝, 長田 裕之, 千葉 奈津子, 柴田 浩行, 岩渕 好治

    日本薬学会年会要旨集 132年会 (2) 119-119 2012/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  103. C5-クルクミノイドの抗腫瘍活性発現にはジエノン構造が重要である

    高山亜紀, 山越博幸, 杉山俊輔, 叶直樹, 石岡千加史, 岩渕好治

    日本薬学会年会要旨集 132nd (2) 2012

    ISSN: 0918-9823

  104. GLO1選択的結合能を有する破骨細胞分化阻害剤methyl gerfelin誘導体の創製

    鈴木貴大, 叶直樹, 高山浩, 川谷誠, 長田裕之, 加藤泰弘, 大島吉輝, 岩渕好治

    日本薬学会年会要旨集 132nd (2) 2012

    ISSN: 0918-9823

  105. Bicyclo[5.3.0]decane型キラル合成素子の開発と応用

    市川龍之介, 川住宗生, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 51st 2012

  106. 新規発蛍光性プローブを用いたNAD+検出法の開発

    守谷崇, 川又綾乃, 高山浩, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 51st 2012

  107. Daphnicyclidin Aの合成研究

    望月綾香, 池田周平, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 132nd (2) 2012

    ISSN: 0918-9823

  108. 抗腫瘍性マクロライドFD-891の合成研究(2)

    川又綾乃, 宮崎雄太, 八幡健三, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 51st 2012

  109. ベンゾフラン類の不斉アザスピロ環化反応を鍵とするfumimycinの合成研究

    澁田拓郎, 佐藤茂樹, 澁谷正俊, 叶直樹, 岩渕好治

    次世代を担う有機化学シンポジウム講演要旨集 10th 2012

  110. ベンゾフラン類の不斉アザスピロ環化反応を鍵とするFumimycinの合成研究

    澁田拓郎, 佐藤茂樹, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 132nd (2) 2012

    ISSN: 0918-9823

  111. アルキンの還元的クロスカップリング反応を用いるheronamide Cの合成研究

    坂西航平, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 132nd (2) 2012

    ISSN: 0918-9823

  112. 抗腫瘍活性天然物irciniastatin Bの全合成研究

    上杉惇一郎, 渡辺翼, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 132nd (2) 2012

    ISSN: 0918-9823

  113. 高活性アルコール酸化触媒AZADOの開発と天然物合成への活用

    岩渕好治, 澁谷正俊, 富澤正樹, 山越博幸, 服部貴宗, 佐藤貴恒, 長田祐二, 笹野裕介, 村上景一, 叶直樹

    天然有機化合物討論会講演要旨集(Web) 54th 2012

    ISSN: 2433-1856

  114. キラルRh(II)触媒を用いた酸化的不斉アミノ化法の開発に基づくchartelline類の合成研究

    澁谷正俊, 佐藤茂樹, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 131st (2) 2011

    ISSN: 0918-9823

  115. キラルRh(II)錯体を用いる3位置換ベンゾフランに対する酸化的不斉アミノ化法の開発研究

    澁田拓郎, 佐藤茂樹, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 131st (2) 2011

    ISSN: 0918-9823

  116. 神経成長因子産生促進作用を有するジテルペノイド(-)-Scabronine Gの不斉全合成

    坂西航平, 飯森絵美子, 西村謙一, 菅原勉, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 131st (2) 2011

    ISSN: 0918-9823

  117. Irciniastatin AによるJNK長期活性化とアポトーシス誘導

    知念拓実, 南雲陽子, 片岡孝夫, 渡辺翼, 今泉貴充, 澁谷正俊, 叶直樹, 岩渕好治, 臼井健郎

    日本農芸化学会大会講演要旨集 2011 2011

  118. 化合物アレイ型プラットフォームを用いたcytochrome P450の基質スクリーニング法の開発

    叶直樹, 高山浩, 高橋俊二, 守谷崇, 川又綾乃, 長田裕之, 岩渕好治

    天然有機化合物討論会講演要旨集 53rd 2011

  119. 抗腫瘍活性天然物irciniastatin Bの全合成研究

    上杉惇一郎, 渡辺翼, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 50th 2011

  120. アンサマクロラクタム抗腫瘍活性天然物cytotrienin Aの合成研究

    佐藤亮, 小松慎悟, 野口昌嗣, 澁谷正俊, 叶直樹, 岩渕好治

    複素環化学討論会講演要旨集 41st 2011

  121. 新規酸化的エーテル化反応を基盤とした8-oxabicyclo[3.2.1]oct-3-en-2-one両対掌体の開発と(+)-sundiversifolideの全合成

    川住宗生, 叶直樹, 岩渕好治

    有機合成化学セミナー講演予稿集 28th 2011

  122. (-)-Scabronine Gの不斉全合成

    坂西航平, 飯森絵美子, 西村謙一, 叶直樹, 岩渕好治

    有機合成化学セミナー講演予稿集 28th 2011

  123. (-)-Scabronine Gの不斉全合成

    坂西航平, 飯森絵美子, 西村謙一, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 50th 2011

  124. HPLC/PDA法を用いた体内動態解析による抗アルツハイマー病天然薬物ノビレチンの脳内移行の証明

    三枝大輔, 中島晶, 鐵尚美, 澁谷正俊, 山越博幸, 岩渕好治, 横須賀章人, 指田豊, 三巻祥浩, 永沼章, 大泉康, 大泉康, 大泉康, 富岡佳久, 山國徹

    日本薬学会年会要旨集 131st (4) 2011

    ISSN: 0918-9823

  125. 生体内transアコニット酸生成機構解明のための有機酸高感度定量法の確立

    松本周平, 三枝大輔, 竹田千尋, 鈴木直人, 澁谷正俊, 岩渕好治, 富岡佳久

    日本薬学会年会要旨集 131st (4) 2011

    ISSN: 0918-9823

  126. 三置換ビニルヨージドとビニルスズ化合物の異常Stilleカップリング反応

    大野裕太郎, 福田隼, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 50th 37 2011

  127. Synthesis and SAR Study of Vicenistatin, an Antitumor 20-Membered Macrolactam Glycoside

    Fukuda Hayato, Nakamura Shiina, Ohno Yutaro, Nishiyama Yuko, Usui Takeo, Eguchi Tadashi, Iwabuchi Yoshiharu, Kanoh Naoki

    天然有機化合物討論会講演要旨集 (52) 385-390 2010/09/01

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.52.0_385  

    More details Close

    In 1993, vicenistatin (1) was isolated as a potent antitumor antibiotic from Streptomyces halstedii HC-34. Structurally, it consists of a 20-membered macrolactem (i.e., vicenilactam) and a unique amino sugar (i.e., vicenisamine). It is reported that vicenistatin (1) exhibits in vitro cytotoxicity against several human cancer cell lines and is effective in a mouse xenograft model. Intrigued with vicenistatin (1) as a potential new cancer therapeutic lead, we initiated a study to uncover its unknown mode-of-action. As a part of this program, we recently accomplished a first-generation total synthesis of vicenistatin (1) using intramolecular Stille coupling as a key step. However, the key intramolecular Stille coupling proceeded in very low yield (-20%). Herein, we report second-generation syntheses of vicenistatin (1) and its analogs using ring-closing metathesis as a key reaction, as well as the structure-activity relationship study of vicenistatins.

  128. 新規クルクミン類縁体はIRF4/MUM1を標的として多発性骨髄腫に対する抗腫瘍効果をもたらす(Novel curcumin analogs have anti-tumor potentials against myeloma cells through the suppression of IRF4/MUM1 function)

    工藤 千枝子, 山越 博幸, 佐藤 温子, 大堀 久詔, 石岡 千加史, 岩渕 好治, 柴田 浩行

    日本癌学会総会記事 69回 399-399 2010/08

    Publisher: 日本癌学会

    ISSN: 0546-0476

  129. 構造活性相関を指向した抗腫瘍活性天然物ビセニスタチンの合成研究

    福田隼, 中村織依菜, 叶直樹, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム 21st 49 2010/06/05

  130. 抗腫瘍活性天然物ビセニスタチンの合成と構造活性相関

    中村織依菜, 福田隼, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 130th (2) 77-77 2010/03/05

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  131. 8-オキサビシクロ[3.2.1]型キラル合成素子の開発研究

    川住宗生, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 130th (2) 2010

    ISSN: 0918-9823

  132. 有機分子触媒を用いた分子内不斉アルドール反応によるキラルビシクロ環構築法の開発研究

    村崎広太, 本澤慶一, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 130th (2) 2010

    ISSN: 0918-9823

  133. 特異的切断サイトを有する新規光親和型小分子アフィニティービーズの開発

    叶直樹, 守谷崇, 高山浩, 本田香織, 照屋貴之, 清水史郎, 長田裕之, 岩渕好治

    日本薬学会年会要旨集 130th (2) 2010

    ISSN: 0918-9823

  134. GO-Y086のプロテオミクス解析を用いた作用標的推測

    室井誠, 野田和恵, 近藤久恵, 山越博幸, 叶直樹, 柴田浩行, 岩渕好治, 長田裕之

    日本農芸化学会大会講演要旨集 2010 2010

  135. Irciniastatin A/psymberinの作用機構解析

    知念拓実, 南雲陽子, 渡辺翼, 今泉貴充, 澁谷正俊, 叶直樹, 岩渕好治, 臼井健郎

    日本農芸化学会大会講演要旨集 2010 2010

  136. キラルAZADO誘導体を触媒とする第2級アルコールの速度論的分割反応の開発と応用

    澁谷正俊, 山越博幸, 富澤正樹, 村上景一, 長田祐二, 叶直樹, 岩渕好治

    反応と合成の進歩シンポジウム講演要旨集 36th 2010

    ISSN: 0919-2123

  137. プルダウンプローブを用いた破骨細胞分化阻害剤Methyl gerfelinと各結合タンパク質群の相互作用解析

    鈴木貴大, 叶直樹, 高山浩, 川谷誠, 長田裕之, 岩渕好治

    日本薬学会東北支部大会講演要旨集 49th 2010

  138. 連続的ヘテロ環形成反応を鍵とするdaphnicyclidin Aの合成研究

    望月綾香, 池田周平, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 49th 2010

  139. アポトーシス誘導活性天然物cytotrienin Aの合成研究

    佐藤亮, 小松慎悟, 野口昌嗣, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 49th 2010

  140. 8-オキサビシクロ[3.2.1]型キラル合成素子の開発研究

    川住宗生, 澁谷正俊, 叶直樹, 岩渕好治

    複素環化学討論会講演要旨集 40th 2010

  141. 構造活性相関を指向した抗腫瘍活性天然物ビセニスタチンの合成研究

    福田隼, 中村織依菜, 叶直樹, 岩渕好治

    反応と合成の進歩シンポジウム講演要旨集 35th (0) 308-309 2009/10/30

    Publisher: Division of Organic Chemistry, The Pharmaceutical Society of Japan

    DOI: 10.14895/hannou.35.0.142.0  

    ISSN: 0919-2123

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    Vicenistatin (1), a potent antitumor antibiotic consisting of a 20-membered macrolactam (vicenilactam) and an amino sugar (vicenisamine), was isolated from Streptomyces halstedii HC-34 by Shindo et al. in 1993. Our aim is to develop efficient synthetic routes to 1 and its derivatives for structure-activity relationship study as well as for identifying molecular target of 1. Amino sugar 2 was synthesized using Sharpless kinetic resolution as a key step. On the other hand, macrolactam 3 was synthesized using Horner-Wadsworth-Emmons reaction (HWE) and cyclization via intramolecular Stille coupling or ring-closing metathesis (RCM) as key steps. Thus, we have accomplished the efficient formal synthesis of 1.

  142. 合成新規クルクミン類縁体の抗腫瘍活性に関する評価 アポトーシス誘導能および転移浸潤抑制能について(The therapeutic potentials about the novel curcumin analogs: apoptosis induction abilities and anti-metastatic effects)

    工藤 千枝子, 山越 博幸, 佐藤 温子, 大堀 久詔, 角道 祐一, 石岡 千加史, 岩渕 好治, 柴田 浩行

    日本癌学会総会記事 68回 465-465 2009/08

    Publisher: 日本癌学会

    ISSN: 0546-0476

  143. 抗腫瘍活性天然物ビセニスタチンの合成研究

    福田隼, 中村織依菜, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 129th (2) 91 2009/03/05

    ISSN: 0918-9823

  144. 抗腫瘍性マクロライドFD‐891の合成研究

    八幡健三, 福田隼, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 129th (2) 92 2009/03/05

    ISSN: 0918-9823

  145. リガンド反応性分子標的を検出・同定する開裂型photoaffinity bead

    高山浩, 叶直樹, 叶直樹, 本田香織, 守谷崇, 照屋貴之, 清水史郎, 長田裕之, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム 20th 2009

  146. 8-オキシビシクロ[3.2.1]型キラル合成素子の開発研究

    川住宗生, 渋谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 48th 2009

  147. 抗腫瘍活性食用植物成分curcuminをリードとする創薬化学研究

    山越博幸, 叶直樹, 大堀久詔, 佐藤温子, 工藤千枝子, 柴田浩行, 岩渕好治

    日本薬学会東北支部大会講演要旨集 48th 2009

  148. KSRP特異的リガンドGO-Y086

    山越博幸, 叶直樹, 上田和則, 昆俊亮, 佐竹正延, 大堀久詔, 工藤千枝子, 佐藤温子, 室井誠, 柴田浩行, 大島吉輝, 千葉奈津子, 長田裕之, 岩渕好治

    メディシナルケミストリーシンポジウム講演要旨集 28th 2009

    ISSN: 0919-214X

  149. 有機分子触媒を用いた分子内不斉アルドール反応によるキラルビシクロ環構築法の開発研究

    村崎広太, 本澤慶一, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 48th 2009

  150. 抗腫瘍活性天然物(+)-irciniastatin A/psymberinの全合成研究

    渡辺翼, 今泉貴充, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 129th (2) 2009

    ISSN: 0918-9823

  151. 抗腫瘍活性天然物(+)-irciniastatin A/psymberinの全合成

    渡辺翼, 今泉貴充, 澁谷正俊, 叶直樹, 岩渕好治

    天然有機化合物討論会講演要旨集 51st 2009

  152. 抗腫瘍活性マクロライドFD‐891の合成研究

    宮崎雄太, 八幡健三, 福田隼, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 48th 27 2009

  153. プロテアソーム阻害活性天然物Salinosporamide Aの合成研究

    佐藤陽介, 富澤正樹, 福田隼, 正木智人, 澁谷正俊, 叶直樹, 岩渕好治

    天然有機化合物討論会講演要旨集 50th (50) 677-682 2008/09/01

    Publisher: Symposium on the chemistry of natural products

    DOI: 10.24496/tennenyuki.50.0_677  

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    Salinosporamide A (1, NPI-0052) was isolated from a marine bacterium of the new genus Salinospora (strain CNB-392) by W. Fenical et al. in 2003. This compound displays remarkable in vitro cytotoxicity towards many tumour cell lines (IC_<50> of approximately 10nM), and its activity appears to be directed to the inhibition of the 20S proteasome. Owing to the potent biological activity and the fascinating inhibitory mechanism, as well as this complex chemical structure, 1 has been an attractive target for the synthetic chemist, and several total synthesis of the metabolite have now been published. Encouraged by the recent SAR studies showing that the chloroethyl moiety of 1 is responsible to the enhanced biological activities compared with omuralide (2), we have continued our studies to develop a convergent route to 1, featuring the intermolecular aldolization to connect the C2-C3 juncture. In the beginning, we started the model studies on the synthesis of 7,8-dihydrosalinosporamide A. The oxazoline 14 was synthesized from commercially available aldehyde 9 via azide 11, on treatment under various aldolization conditions, 14 brought about retro-Dieckmann decomposition. To avoid this pitfall, we converted keto ester 14' to ketone 17, which was subjected to Reformatsky reaction developed by Honda et al. to give 18a and 18b as a 1:1 stereoisomeric mixture. DBU-induced epimerization at C2 position afforded 18b from 18a in excellent yield After leading 18b to 21 in 5 steps, the treatment of diol 21 with 1-MeAZADO/PhI(OAc)_2 system provided β-lactone in one step, thereby confirming the feasibility of our strategy. Chiral azide 28 was synthesized from (S)-methyl lactate via 13 steps sequence (total 16 steps) involving Ireland-Claisen reaction, RCM using the 1st Grubbs catalyst We also developed more efficient route: oxazoline 35 was elaborated from (R)-Garner aldehyde via 10 steps. The details of the synthesis and progress toward the total synthesis of salinosporamide A will be discussed.

  154. 新規クルクミン誘導体によるCOX2発現抑制と抗腫瘍効果に関する検討(More potent reregulation of COX-2 expression with new curcmin analogue)

    佐藤 温子, 山越 博幸, 工藤 千枝子, 大堀 久詔, 角道 祐一, 石岡 千加史, 岩渕 好治, 柴田 浩行

    日本癌学会総会記事 67回 262-262 2008/09

    Publisher: 日本癌学会

    ISSN: 0546-0476

  155. 新規クルクミンアナログにおける構造機能相関の解析(Analyses of the structure-function relationship of new curcumin analogues)

    工藤 千枝子, 山越 博幸, 佐藤 温子, 大堀 久詔, 角道 祐一, 石岡 千加史, 岩渕 好治, 柴田 浩行

    日本癌学会総会記事 67回 349-349 2008/09

    Publisher: 日本癌学会

    ISSN: 0546-0476

  156. 新規クルクミン類縁体化合物の担癌マウスにおける抗腫瘍活性(Anti-tumor activity of newly synthesized curcumin analogues in vivo)

    柴田 浩行, 山越 博幸, 佐藤 温子, 大堀 久詔, 角道 祐一, 工藤 千枝子, 石岡 千加史, 岩渕 好治

    日本癌学会総会記事 67回 349-349 2008/09

    Publisher: 日本癌学会

    ISSN: 0546-0476

  157. 抗腫瘍活性天然物ビセニスタチンの構造活性相関を指向した合成研究 2

    中村織依菜, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 47th 2008

  158. Huperzine Aの合成研究

    五十嵐史也, 後ノ上健太, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 47th 2008

  159. 神経成長因子産生促進作用を有するジテルペノイドscabronine Gの不斉全合成研究

    飯森絵美子, 西村謙一, 池田周平, 叶直樹, 菅原勉, 岩渕好治

    日本薬学会年会要旨集 128th (2) 2008

    ISSN: 0918-9823

  160. Chartelline Aの不斉全合成研究

    佐藤茂樹, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 128th (2) 2008

    ISSN: 0918-9823

  161. (+)-Daphnicyclidin Aの全合成研究

    池田周平, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会年会要旨集 128th (2) 2008

    ISSN: 0918-9823

  162. 海洋産アルカロイドchartelline Aの不斉全合成研究

    佐藤茂樹, 澁谷正俊, 叶直樹, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム 19th 2008

  163. プロリン型有機分子触媒を用いた不斉アルドール反応によるキラルビシクロ環構築法の開発研究

    本澤慶一, 板垣徳晃, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 47th 2008

  164. 抗腫瘍活性天然物ビセニスタチンの構造活性相関を指向した合成研究 1

    福田隼, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 47th 21 2008

  165. 新規合成クルクミン誘導体による大腸癌発癌予防効果に関する検討(Chemopreventive Effects of New Curcumin Analogs against Colorectal Carcinogenesis)

    柴田 浩行, 佐藤 温子, 大堀 久詔, 角道 祐一, 岩渕 好治, 石岡 千加史

    日本癌学会総会記事 66回 181-181 2007/08

    Publisher: 日本癌学会

    ISSN: 0546-0476

  166. 家族性腫瘍の1次予防から3次予防について 食品に由来する化合物の新規類縁体を用いた化学発癌予防

    柴田 浩行, 大堀 久詔, 角道 祐一, 佐藤 温子, 岩渕 好治, 石岡 千加史

    家族性腫瘍 7 (2) A23-A23 2007/05

    Publisher: 日本家族性腫瘍学会

    ISSN: 1346-1052

  167. (-)‐カイニン酸の実用合成法の開発研究

    富澤正樹, 鈴木裕行, 福田隼, 岩渕好治

    日本薬学会年会要旨集 127th (4) 22 2007/03/05

    ISSN: 0918-9823

  168. Nobiletin類縁合成フラボノイドの細胞内情報伝達系に対する作用

    丸山 裕二, 山國 徹, 松崎 健太郎, 山越 博幸, 澁谷 正俊, 岩渕 好治, 大泉 康

    日本薬学会年会要旨集 127年会 (2) 95-95 2007/03

    Publisher: (公社)日本薬学会

    ISSN: 0918-9823

  169. 抗腫瘍活性天然物(-)-cylindrocyclophane Aの全合成とその構造活性相関

    五十嵐史也, 山越博幸, 南昌孝, 菅原勉, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 46th 2007

  170. 抗腫瘍活性食用植物をリードとする創薬化学研究

    山越博幸, 富澤正樹, 澁谷正俊, 大堀久詔, 柴田浩行, 叶直樹, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム 18th 2007

  171. 抗腫瘍活性天然物(+)-irciniastatinA/psymberinの全合成研究

    渡辺翼, 今泉貴充, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 46th 2007

  172. 新規プロリン型有機分子触媒を用いたキラルビシクロ環構築法の開発研究

    本澤慶一, 板垣徳晃, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 46th 2007

  173. Salinosporamide Aの合成研究

    佐藤陽介, 富澤正樹, 福田隼, 正木智人, 澁谷正俊, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集 46th 29 2007

  174. An enantio- and diastereocontrolled synthesis of (+)-7-deoxy-trans-dihydronarciclasine (vol 66, pg 167, 2005)

    T Fujimura, M Shibuya, K Ogasawara, Y Iwabuchi

    HETEROCYCLES 68 (2) 451-451 2006/02

    ISSN: 0385-5414

  175. Expedient synthesis of potent cannabinoid receptor agonist (-)-CP55,940 (vol 7, pg 4181, 2005)

    N Itagaki, T Sugahara, Y Iwabuchi

    ORGANIC LETTERS 7 (21) 4785-4785 2005/10

    ISSN: 1523-7060

  176. 87(P-22) Development of a catalytic asymmetric Baylis-Hillman reaction and its application to natural product synthesis

    Nakano Ayako, Kawahara Sakie, Furukawa Mariko, Ushiyama Mina, Sugihara Tatsuya, Nakatani Mari, Esumi Tomoyuki, Iwabuchi Yoshiharu, Hatakeyama Susumi

    Symposium on the Chemistry of Natural Products, symposium papers 44 (0) 509-514 2002

    Publisher: Symposium on the Chemistry of Natural Products Steering Committee

    DOI: 10.24496/tennenyuki.44.0_509  

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    Development of a simple and reliable method for the construction of multifunctional molecules starting from readily available starting materials is of great importance in synthetic organic chemistry. In this regard, the Baylis-Hillman reaction, tertiary amine-catalyzed C-C bond-forming reaction of an aldehyde with an acrylate, has attracted considerable attention. We have recently discovered a reliable asymmetric Baylis-Hillman reaction, which utilizes (3R,8R,9S)-10,11-dihydro-3,9-epoxy-6&#039;-hydroxy-cinchonane (β-cupreidine) as a chiral amine catalyst and 1,1,1,3,3,3-hexafluoroisopropyl acrylate as an activated alkene. This method allows conversion of a wide variety of aldehydes to the corresponding (R)-(α-methylene-β-hydroxy)esters with high enantiomeric excess in reasonable yields. We describe here the structure-function relationship of the amine catalyst as well as the scope and limitation of the reaction. We also present the preliminary result on the synthesis of a new catalyst, which acts as a pseudo-enantiomer of β-cupreidine to give (S)-(α-methylene-β-hydroxy)esters. Furthermore, we discuss enantio-, and stereocontrolled syntheses of mycestericin E and epopromycin B, biologically interesting natural products, by stereoselective functionalization of the Baylis-Hillman adducts.

  177. The first observation of the [Cp3Mn]2 anion; structures of hexagonal [(η2-Cp)<inf>3</inf>MnK·1.5thf] and ion-separated [(η2-Cp)3Mn]<inf>2</inf>[Mg(thf)<inf>6</inf>]·2thf

    Yoshiharu Iwabuchi, Mariko Furukawa, Tomoyuki Esumi, Susumi Hatakeyama

    Chemical Communications 1 2030-2031 2001/01/01

    DOI: 10.1039/b106471c  

    ISSN: 1359-7345

  178. 38 Total Synthesis of Trachyspic Acid, a Tumor Cell Heparanase Inhibitor

    Hirai Kanako, Ooi Hidenori, Esumi Tomoyuki, Iwabuchi Yoshiharu, Hatakeyama Susumi

    Symposium on the Chemistry of Natural Products, symposium papers 43 (0) 223-228 2001

    Publisher: Symposium on the Chemistry of Natural Products Steering Committee

    DOI: 10.24496/tennenyuki.43.0_223  

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    Trachyspic acid was isolated from the culture broth of Talaromyces trachyspermus SANK 12191 after screening for low molecular weight substances that exhibit heparanase inhibitory activity. This new metabolite possesses a unique spiroketal structure consisting of the 2-nonyl-3-furanone and the tetrahydrofuran having citric acid unit. However, even the relative configuration of this compound has not been determined yet. We describe the first synthesis of (±-trachyspic acid, thereby establishing its relative configuration to be 3R^*4S^*6S^*. Aldol reaction of tert-butyl 4-(p-methoxybenzyl)oxy-2-oxo-butyrate (9) and tert-butyl 4-pentenoate (10) gave (3R^*,4S^*)-11a and (3R^*,4S^*)-11b in a ratio of 3: 2. Upon silylation and oxidative cleavage of the olefinic double bond, 11a and 11b were converted to key aldehydes 12a and 12b, respectively. The crucial Ni(II)/Cr(II)-mediated reaction of 12a with triflate 16, prepared from 3-(1,3-dioxolan-2-yl)dodecan-2-one (15), turned out to occur successfully to produce adduct 17a in 84% yield. Similarly, Ni(II)/Cr(II)-mediated reaction of 12b with 16 afforded 17b in 59% yield. Upon Dess-Martin oxidation, desilylation, and HClO_4-treatment, 17a and 17b gave the corresponding spiroketal 19a and 19b in very good yields. After acetylation of 19a and 19b, the corresponding acetates were each converted to ketone 22a and 22b by a three-step sequence involving removal of the p-methoxybenzyl protecting group, oxidation of the primary alcohol, and ozonolysis of the exomethylene group. Finally, exposure of 22a and 22b to TFA furnished the corresponding tricarboxylic acid 23a and 23b, respectively. At this stage, we found that 23b was identical with trachyspic acid by ^1H NMR comparison. The trimethyl ester of 23b also exhibited spectral properties in accord with those reported for the trimethyl ester of natural trachyspic acid.

  179. 108(P-32) Synthetic Study on Antitumor Natural Product, Fostriecin (CI-920)

    Esumi Tomoyuki, Okamoto Nanako, Iwabuchi Yoshiharu, Hatakeyama Susumi

    Symposium on the Chemistry of Natural Products, symposium papers 42 (0) 643-647 2000

    Publisher: Symposium on the Chemistry of Natural Products Steering Committee

    DOI: 10.24496/tennenyuki.42.0_643  

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    Fostriecin (1), a novel antibiotic produced by Streptomyces pulveraceus, displays efficacious in vivo antitumor activity against L1210 leukemia in mice and the phase I clinical trials have already started at NCI for developing a new anticancer drug. This compound has a very unique structure characterized by the α,β-unsaturated δ-lactone with the highly oxygenated long chain containing C9-phosphate ester, C8-quaternary center, and conjugated (12Z,14Z,16E)-triene. Recently, its absolute configuration was determined to be (5R,8R,9R,11R) by Boger and co-workers. We describe here an enantioselective synthesis of the 8,9-acetonide of dephosphorylated fostriecin, a promising precursor for the synthesis of fostriecin (1). We first focused on Sharpless asymmetric dihydroxylation of two conjugated dienes 13 and 18 to construct the (8R,9R)-diol functionality. Upon treatment of 13 with AD-mix-β, regio- and diastereoselective dihydroxylation took place at the tri-substituted double bond to afford (8R,9R)-diol 14 as a major product. Interestingly, the dihydroxylation of 18 was found to proceed with complete regio- and diastereoselectivity to give (8R,9R)-diol 19 exclusively. After conversion of 14 to aldehyde 25, we then proceeded to install the C12-C18 chain having (12Z,14Z,16E)-triene. When 25 was reacted with the alkenyllithium prepared from 24, the desired product 26 was obtained as 2:1 epimeric mixture in very poor yield. However, we were gratified to find that palladium catalyzed Stille coupling of alkenyl iodide 30, prepared from 25, with butadienylstannane 31 proceeded very smoothly to produce 32 almost quantitatively. Compound 32 thus obtained is the 8,9-acetonide of dephosphorylated fostriecin.

  180. 3 Total Synthesis of (-)-Dysiherbaine, a New Marine Neurotoxin, and its Congener (+)-Lycoperdic Acid

    Masaki Hidekazu, Maeyama Junji, Kamada Kazuko, Iwabuchi Yoshiharu, Hatakeyama Susumi

    (41) 13-18 1999/09/01

    Publisher: Symposium on the chemistry of natural products

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    (-)-Dysiherbaine was isolated from a Micronesian sponge Dysidea herbacea after screening for substances that exhibit potent neurotoxic activity. This amino acid was found to be a selective agonist of non-NMDA type glutamate receptors in CNS. Although the relative structure was determined to be a novel di-amino di-carboxylic acid having a densely substituted pyran ring fused with 2-amino-3-(2'-carboxy-5'-tetrahydrofuranyl)propanoic acid, its absolute structure remains unsolved. (+)-Lycoperdic acid, isolated from the mashroom Lycoperdon perlatum, is the 5'-oxo analogue of 2-amino-3-(2'-carboxy-5'-tetrahydrofuranyl)propanoic acid which is the core structure of dysiherbaine. We describe here a novel enntiocontrolled synthesis of (+)-lycoperdic acid and the first total synthesis of (-)-dysiherbaine based on the strategy involving four major transformations; (i) palladium catalyzed cross-coupling reaction of the organozinc reagent, prepared from a β-iodo alanine derivative, with an alkenyl iodide or triflate, (ii) diastereoselective epoxidation, (iii) acid catalyzed cyclization, (iv) oxidation. The present synthesis of (-)-dysiherbaine allows us to conclude that the absolute configuration of natural dysiherbaine is (2S,4R,6R,7R,8R,9S).

  181. 69(P48) Synthesis of Viridiofungin A and its Absolute Structure

    Esumi T, Iwabuchi Y, Irie H, Hatakeyama S

    Symposium on the Chemistry of Natural Products, symposium papers 39 (0) 409-414 1997

    Publisher: Symposium on the Chemistry of Natural Products Steering Committee

    DOI: 10.24496/tennenyuki.39.0_409  

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    Viridiofungin A was isolated from a strain of Trichoderma viride Pers. (Fungi, Hyphomycetes) together with viridiofundin B and C after screening for substances that exhibit cholesterol lowering activity. These viridiofungins, a novel family of squalene synthase inhibitors, have unique structures consisting of a common citric acid moiety having C-16 long chain and an aromatic amino acid residue such as tyrosine, phenylalanine, and tryptophane. However, the absolute structures of these compounds have not been determined yet. We describe the first synthesis of viridiofungin A trimethyl ester which allowed us to determine its absolute configuration to be 3S,4S,2&#039;S. Katsuki-Sharpless asymmetric epoxidation of the trisubstituted allylic alcohol 11 followed by regio- and stereoselective opening of epoxide to give the diol 13 from which two epimeric aldehydes 14 and 25 were prepared selectively. Upon attachment of the long chain portion by Wittig olefination reaction followed by functional group transformations, the aldehyde 14 and 25 gave the alcohol 21 and 26 respectively. After Jones oxidation of 21, the resulting carboxylic acid was condensed with L- and D-tyrosine methyl ester to give (3S,4S,2&#039;S)-viridiofungin A trimethyl ester (22) and (3S,4S,2&#039;R)-viridiofungin A trimethyl ester (23). Similarly, (3S,4R,2&#039;S)-viridiofungin A trimethyl ester (27) and (3S,4R,2&#039;R)-viridiofungin A trimethyl ester (28) were also synthesized from 26. Now we can conclude that the absolute configuration of natural viridiofungin A is 3S,4S,2&#039;S by comparison (^1H NMR and TLC) of four synthetic samples with natural viridiofungin A trimethyl ester in addition to information that the tyrosine-configuration is L.

  182. REGIOSELECTIVE AND STEREOSELECTIVE DEPROTECTION OF ACYLATED CARBOHYDRATES VIA CATALYTIC ANTIBODIES

    FUJII, I, Y IWABUCHI, H MIYASHITA, R TANIMURA, K KINOSHITA, M KIKUCHI

    JOURNAL OF CELLULAR BIOCHEMISTRY 194-194 1994

    ISSN: 0730-2312

  183. COMPLEX OLIGOSACCHARIDE SYNTHESIS

    CW HUMMEL, NJ BOCKOVICH, Y IWABUCHI, T SUZUKI, KC NICOLAOU

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 203 28-BTEC 1992/04

    ISSN: 0065-7727

  184. A FACILE SYNTHESIS OF (R)-1-BENZYLOXY-3-BUTEN-2-OL

    S TAKANO, S TOMITA, Y IWABUCHI, K OGASAWARA

    SYNTHESIS-STUTTGART (8) 610-611 1988/08

    ISSN: 0039-7881

Show all ︎Show first 5

Research Projects 30

  1. 有機ニトロキシルラジカルー遷移金属協奏触媒の機能創成を機軸とする精密有機分子構築

    岩渕 好治, 笹野 裕介, 山越 博幸, 長澤 翔太

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 基盤研究(B)

    Institution: 東北大学

    2022/04/01 - 2025/03/31

  2. ゲノムワイドCRISPRスクリーニング法を用いた糖尿病性腎症の新規創薬・病態解明

    菅原 明, 岩渕 好治, 横山 敦

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 挑戦的研究(萌芽)

    Institution: 東北大学

    2021/07/09 - 2023/03/31

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    我々は、当該年度の下記の成果を得た。 1)D532の標的遺伝子の解析:我々は野生型マウス群、1型糖尿病性腎症モデルマウスであるiNOS-トランスジェニック(TG)マウス+Vehicle群、iNOS-TGマウス+D532群の各腎臓から抽出したRNAを用いて、RNA-Sequenceを施行した。その結果、Lpk、Fis1、Kcnb1、Dguok、Slc25a15といったChREBPの標的遺伝子に加えて、Txnipも野生型マウス群に比してiNOS-TGマウス群でその発現が著明に増加していた一方で、iNOS-TGマウス+D532群では発現が顕著に減少していることが明らかとなった。また、GO enrichment analysisでも細胞内シグナル伝達経路やアポトーシス経路の有意な変動が観察された。以上の結果から、TxnipがD532の下流に存在することが確認された。現在、更なるパスウェイ解析を行うことにより、D532作用時の腎臓におけるTxnipの上流遺伝子を検索中である。2)CRISPR-Cas9システムによるChREBP KOマウスの作成:ChREBPのDNA結合ドメインであるヘリックス-ループ-ヘリックス構造(Exon 13~14内)を含むExon 12からExon 14を認識するcrRNAを作製し、マウス受精卵(B6N×B6N)に対してエレクトロポレーション法によりCas9 protein 100 ng/μL、100 ng/μL crRNAs、100 ng/μL tracrRNAを導入した。作製した受精卵は偽妊娠雌マウスの卵管に導入し、変異マウスは胎生19日目に出生した。得られたChREBP KOマウス腎臓でのChREBP欠損はWestern blotによって確認された。

  3. 糖質応答転写因子ChREBPを標的とした糖尿病性腎症の病態解明・新規創薬

    菅原 明, 岩渕 好治, 横山 敦, 岡本 好司

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 基盤研究(B)

    Institution: 東北大学

    2020/04/01 - 2023/03/31

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    我々は当該年度に以下の実験を遂行した。 1)糖尿病性腎症(DN)の発症・増悪におけるChREBPの関与・作用機構の解明:A) CRISPR/Cas9システムを用いて作成したChREBPノックアウトマウスからRNAを抽出してRNAシークエンスに供する準備を進めている。B)東北大学医学部倫理委員会にて承認を得たことから、東北大学病院 腎・高血圧・内分泌科の腎生検組織からのRNA抽出・RNAシークエンスに向けて、DNならびに非DN検体の準備を進めている。 2)D532のDN改善効果の機序解明および実用化・臨床応用に向けた構造最適化:A)D532の一端を伸長して末端をビオチン化することにより作成したD532プローブを用いて、アビジン‐ビオチン反応を利用したアフィニティ精製・質量分析にてD532の標的因子の同定を進めた結果、ChREBP自身がD532の標的因子であることが明らかとなった。B)ChIPアッセイの結果、D532がChREBPのDNAへの結合を抑制することが認められた。本結果から、D532が高血糖依存性のChREBP転写活性をDNA結合レベルで抑制することが明らかとなった。C)D532はChREBPの核内移行には影響を及ぼさないことが明らかとなった。D)疎水性であるD532をPMB30Wにてミセル化することにより水溶化が出来ることが明らかとなった。本成果により、今後のD532を用いた非臨床試験・臨床試験に向けて大きく前進できるものと期待される。

  4. Synthesis and structural diversification of induced pluripotent stem molecules based on polyene macrolactam natural products

    Kanoh Naoki

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (C)

    Institution: Hoshi University

    2019/04/01 - 2022/03/31

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    This study aims to design and synthesize polyene macrolactam-based induced pluripotent synthetic small molecules (iPS molecules) that diversify into polycyclic compounds, each having a different skeleton and biological activity in response to various stimuli, such as light irradiation and oxidative conditions, and so on. To apply the reactivity of marine-derived polyene macrolactam heronamide C to the induced pluripotent small molecules, we firstly developed a modular synthetic strategy for the heronamide C-type polyene macrolactams. Then, various heronamide C derivatives were synthesized by using the developed strategy. Evaluation of their reactivity clarified structural factors needed for selective structural diversification.

  5. Precise construction of organic molecules based on organonitroxyl radical-transition metal hybrid catalysts

    Iwabuchi Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2019/04/01 - 2022/03/31

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    We have developed novel organo-nitroxyl radical-transition metal catalyst hybrid catalysts that enable aerobic oxidative molecular transformations under room temperature with the activation of molecular oxygen. As a result, we were able to develop reaction conditions for oxidation of vic-amino alcohols to give either the corresponding carbonyl compound or one-carbon degradated product. On the other hand, in pursuit of catalytic intramolecular phenol coupling reactions, we were able to establish a novel reaction system in which the desired intramolecular dearomatizing phenol coupling reaction proceeds by the combination of an organonitroxyl radical and a Cr-salen complex.

  6. Development of highly enantioseletive aerobic alcohol oxidation system based on chiral AZADO-Cu cooperative catalysis

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

    Institution: Tohoku University

    2018/04/01 - 2020/03/31

  7. Development of nitrogen-containing versatile chiral building blocks driven by novel chemoselctive catalysis

    Iwabuchi Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2016/04/01 - 2019/03/31

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    We have developed an exceptionally chemoselective aerobic alcohol oxidation using AZADO/copper catalysis, which allows the presence of oxidation-labile functional groups, e.g. unprotected amino- and divalent sulfur groups. Based on the AZADO/copper system, a chirally modified AZADO has been designed to identify chemo- and enantioselective aerobic OKR of aliphatic secondary alcohols. We have also disclosed that Ln(OTf)3 enables catalytic intramolecular aminolysis of 3,4-epoxy-1-amines to give 2-substituted 3-hydroxypyrrolidines via unprecedented 5-endo-tet mode of cyclization.

  8. AZADO-Cu協奏触媒の高度機能化による高難度アルコール選択的空気酸化

    岩渕 好治

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 新学術領域研究(研究領域提案型)

    Institution: 東北大学

    2016/04/01 - 2018/03/31

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    本研究は、研究代表者らが最近見出した新規で有用な化学選択性を発現する触媒システム、すなわち「無保護アミノアルコールのアルコール選択的酸化」を常温・常圧の大気下という温和な条件下で実現するAZADO-Cu協奏触媒への精密機能修飾を機軸として、分子複雑系における高難度アルコール選択的空気酸化反応の開発を行うとともに、その合成化学的有用性を実証することを目的とするものである。 計画研究の2年目に当たる平成29年度は、前年度までに見出していた不斉配位子複合型ニトロキシルラジカルによる第2級アルコールの酸化的速度論的光学分割のエナンチオ選択性発現機構の理解と選択性の向上を目指して検討を行った。 現時点で90% eeという不斉収率を与えるtrans-2-フェニル-1-シクロヘキサノールを基準基質として、その分子骨格を変化させた基質について検討行った。相対立体配置をcisとした基質ではエナンチオ選択性が発現せず、シクロヘキサノール2位の置換基については、アルキル基、エーテル基、エステル基が許容であることが判明した。驚くべきことに、シクロペンタン骨格とした基質では反応が全く進行せず、反応後に原料が回収されたことから、厳密な基質認識が行われていることが示唆された。鎖状アルコールでは、水酸基のβ位に嵩高い置換基を有する場合に、中程度のエナンチオ選択性で分割されることが確認された。これらの新知見をもとに、不斉配位子複合型ニトロキシルラジカル-Cu協奏触媒の反応機構モデルを構築して計算化学の観点から検証を行い、基質適用性の拡大とエナンチオ選択性向上に資する有望な触媒設計指針を得ることができた。

  9. Challenge toward controlling oxidative phenol coupling reaction by AZADO-Cu cooperative catalysis

    Iwabuchi Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Challenging Exploratory Research

    Institution: Tohoku University

    2016/04/01 - 2018/03/31

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    On the basis of our original aerobic catalytic alcohol oxidation system consisting of AZADO/CuCl/bipyridy/DMAP, we have challenged to discover another catalytic system that enables highly chemo- and regioselective phenol coupling reactions. As a result, we identified that combination of AZADO-Cr promoted an intramolecular coupling of 3-(3-(4-hydroxyphenyl)propyl)phenol to give the corresponding tricyclic product. We also disclosed that AZADO/CuCl/bipyridyl/DMAP system realized a highly chemoselective aerobic oxidation of sulfide-containing alcohols, providing a useful addition to AZADO oxidation technology.

  10. Pharmacological potential of curcumin analog targeting KSRP, a regulator of miRNA

    Shibata Hiroyuki, IWABUCHI Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (C)

    Institution: Akita University

    2013/04/01 - 2016/03/31

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    Effects on mRNA and miRNA by curcumin analogs, GO-Y030 and GO-Y078, were examined. BCL-2, c-Myc and p53 were included in the affected transcripts by GO-Y030 among 41,058 transcripts in colorectal cancer cell line. Among 2,669 species of miRNAs in colorectal cancer cell line, 28 species and 11 species of miRNAs were up-regulated by GO-Y030 and GO-Y078, respectively. In endothelial cells, 470 species of mRNAs were up-regulated and 243 species were down-regulated. As for miRNA, has-miR-19b-3p was up-regulated in endothelial cells by GO-Y030, and 5 species of miRNAs were down-regulated by GO-Y078. KSRP contribution to the regulation of mRNA or miRNA expression was not elucidated at this present.

  11. Eco-benign Synthesis of Versatile Chiral Building Blocks Driven by Organocatalysis

    Iwabuchi Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

    Institution: Tohoku University

    2011/04/01 - 2016/03/31

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    Natural products having a fused seven membered ring often elicit fascinating biological activities and pose considerable challenges to synthetic community. In order to enrich the strategic latitude for assembling medicinally relevant cycloheptanoid and hydroazulenoid structures, we have developed enantioselective routes to versatile cycloheptanoid chiral building block, namely, 4-hydroxy-cyclohept-2-en-1-one and 8-oxabicyclo[3.2.1]oct-3-en-2-one, driven by the use of organocatalysis. To facilitate a multistep synthetic transformations involving alcohol oxidations, we have also developed a series of nitroxyl radical-type organocatalysts that offer highly efficient and selective oxidation alcohols under eco-friendly reaction conditions.

  12. Development of prodrugs based on a controlled reversible Michael reactions

    IWABUCHI Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Challenging Exploratory Research

    Institution: Tohoku University

    2013/04/01 - 2015/03/31

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    C5-curcuminoids are antitumor curcumin analogues bearing a reactive cross conjugated dienone structure. Dienone moiety is thought to be essential for antitumor activity and act as a Michael acceptor, which is traditionally avoided by medicinal chemists. Focusing on the dienone system, we monitored Michael reaction and retro Michael reaction between GO-Y030 and cysteamine by 1H-NMR spectroscopy method. In addition, we synthesized C5-curcuminoid thiol-adducts and evaluated their cell growth inhibitory activity against human colon cancer HCT116. The cytoxicity of C5-curcuminoid thiol-adduct was almost comparable with that of GO-Y030, highlighting their potential as prodrugs. Our results indicated that C5-curcuminoids react with cysteine thiol in a reversible manner, which is considered as important intracellular behavior of C5-curcuminoid.

  13. Development of aerobic alcohol oxidation systems based on nitroxyl radical-Cu catalysis

    IWABUCHI Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2012/04/01 - 2015/03/31

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    We have successfully developed the highly chemoslective aerobic alcohol oxidation using nitroxyl radical-copper catalysis that realize an efficient transformation of an unprotected amino-alcohol into the corresponding amino-carabonyl compound. We have identified the optimum combination of nitroxyl radical, copper salt, and solution concentration dependent on the type of substrate. Useful information of the catalyst structure-enantioselectivity relationship has been obtained, which will lead the development of an enantioselective aerobic oxidation system.

  14. Novel Oxidative Synthetic Transformations Driven by Chiral Oxoammmonium Salts

    IWABUCHI Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Challenging Exploratory Research

    Institution: Tohoku University

    2011 - 2012

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    Novel synthetic use of azaadamantane-type oxoammonium salts has been exploited. It was found that 9-nor-azaadamantane N-oxy (Nor-AZADO) gives the corresponding oxoammonium salts that exhibit superior activities to AZADO derived oxoammonium salts. Several novel oxidative transformations using Nor-AZADO have been developed including (1) silyl enol ethers to a,b-unsaturated ketones and (2) silyl enol ethers to 1,2-diketones.

  15. Development of a new cancer chemotherapy by using curcumin analogs

    SHIBATA Hiroyuki, IWABUCHI Yoshiharu, UEHARA Yoshihiko, OHORI Hisatsugu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (C)

    Institution: Akita University

    2010 - 2012

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    We have developed 86 types of new curcumin analogs, successfully resulting in getting several analogs with higher anti-cancer potential. These analogs are effective for various cancers including colorectal cancer stem cells. They are shown to be NF-κB inhibitors. In animal models, they were also shown to be effective for some cancers such as gastric cancers and colorectal cancer stem cells. These data indicate that new curcumin analogs have some potential to treat cancers.

  16. Drug development targeting for regeneration of neurovascular units in neurodegenerative disorders

    FUKUNAGA Kohji, IWABUCHI Yoshiharu, ITO Yoshihisa, MORIGUCHI Shigaki

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2010 - 2012

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    ST101 stimulates memory molecule, Ca2+/calmodulin-dependent protein kinase II (CaMKII) in the hippocampus. In the present study, we investigated whether chronic administration of the neurovascular regenerative compound, ST101 elicits long lasting ameliorating effects on brain functions and defined the molecular mechanism underlying their therapeutic effects in the neurodegenerative disorders. ST101 was now under investigation in Phase II clinical trial of U.S.A. We defined T type voltage-gated calcium channel as molecular target of ST101. We next introduced novel and potent derivative, SAK3 by using neuro2A cells overexpressing T type voltage-gated calcium channel. This is the first discovery of activators of T type voltage-gated calcium channel in the world. The most promising evidence in our studies is that T type calcium channel is novel therapeutic target of Alzheimer therapy to restore the neural networks in the neurodegenerative disorders.

  17. Development of oxoammonium-salt-type catalysts for highly enantioselective oxidation of alcohols

    IWABUCHI Yoshiharu, SHIBUYA Masatoshi

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2009 - 2011

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    We have developed organocatalytic highly enatiolselecitve oxidation of alcohols based on chiral modifications of 2-azaadamantane N-oxy (AZADO)-derived oxoammonium salts. The chiral AZADOs enabled a highly enantioselecitive kinetic oxidation of racemic secondary alcohols with a broad substrate applicability.

  18. 有機ニトロキシルラジカルをモチーフとする酸化ストレス防御活性薬剤の創製

    岩渕 好治, 福田 隼, 澁谷 正俊

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 挑戦的萌芽研究

    Institution: 東北大学

    2008 - 2009

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    本研究は、酸化ストレスから脳を保護する薬剤としてのアザアダマンタン型有機ニトロキシルラジカル(2-azaadamantne N-oxyl,以下AZADOと略記する)誘導体の潜在的機能性の開発と検証を企図したものである。 本年度は、当研究室で開発した精密修飾アザアダマンタン合成法を活用して、昨年まで未検討となっていた1,4-ジ置換型有機ニトロキシルラジカル7種類ならびに、それらの還元型誘導体であるヒドロキシルアミン7種類を新たに合成することができた。また、その途上で、アザアダマンタン核5位を高効率で酸化修飾する新規知見を得て、これより5-置換AZADOを5種類合成することができた。そして、新たに合成したAZADO類の酸化還元特性について検討を行った結果、1,4-ジ置換型AZADO類は、TEMPOおよびAZADOよりも速やかに、種々の活性酸素(次亜塩素酸、一酸化窒素、スーパーオキシドアニオン)をクエンチする活性を備えていることを確認できた。しかし、被酸化体であるオキソアンモニウムイオンが無置換AZADOに比べて不安定となるためか、反応効率の経時的低下が観測された。上記成果は、水溶性AZADO誘導体の設計に有用な指針を与えるものと考えている。一方、5-ハロ-AZADOは、NOとO2存在下にアルコール類や糖類の触媒的酸化を顕著に促進することを確認し、5-ハロ-AZADO類の触媒的抗酸化剤としての可能性を新たに見出すことができた。

  19. Development of novel neuroprotective drugs targeting for neurovascular unit therapy.

    FUKUNAGA Kohji, IWABUCHI Yushiharu, MORIOKA Motohiro, KASAHARA Jiro, MORIGUCHI Shigeki, SHIODA Norifumi

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2007 - 2009

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    We have introduced novel neuroprotective drugs including calmodulin antagonist DY-9760e and protein kinase B (Akt) activator VO (OPT) in the ischemic neurodegeneration. However, the mechanisms underlying neurovascular unit protection by these compounds remain unclear. We found that DY-9760e and its active metabolite, DY-9836 are potent inhibitors of calcium/calmodulin dependent nitric oxide synthase (NOS) in vivo. We here defined pathophysiological role and mechanism of superoxide generation through uncoupled eNOS in phenylephrine (PE)-induced hypertrophic cardiomyocytes. In PE-induced hypertrophic cardiomyocytes, the superoxide generation was associated with increased uncoupling state of eNOS. Thus, uncoupling of eNOS accounts for superoxide generation by prolonged PE exposure, thereby inducing apoptotic cell death. Furthermore, cardioprotective effects of DY-9836 well correlated with inhibition of aberrant superoxide generation by suppression of eNOS activity. DY-9836 treatment also protected cardiomyocytes from breakdown of caveolin-3/dystrophin, which are major components to scaffold eNOS in cardiomyocyte caveolae. Similarly, DY-9836 treatment also attenuated superoxide generation following brain ischemia by uncoupled eNOS in vascular endothelial cells. Thus the inhibition of superoxide production by DY-9760e/DY9836 is critical for protection of neurovascular units in ischemia-induced neurodegenaration. Neurogenesis is well documented in the subgranular zone (SGZ) of hippocampus. Especially, in the hippocampal neurogenesis, fundamental role of neurogenesis in learning and memory formation has been addressed. We here assessed whether VO (OPT), a stimulator of phosphatidylinositol 3-kinase (PI3K)/Akt and extracellular signal regulated kinase (ERK) pathways promotes neurogenesis following brain ischemia using a mouse transient middle cerebral artery occlusion (MCAO) model. Intraperitoneal administrations of VO (OPT), which is a potent inhibitor for protein tyrosine phosphatases (PTPs), stimulated neurogenesis in the adult dentate gyrus (DG) following brain ischemia. VO (OPT) led to activation of PI3K/Akt and ERK pathways, which are inhibited by treatment with specific inhibitor, wortmannin or U-0126, respectively. Each treatment of them significantly inhibited the neurogenesis, suggesting that both pathways need to elicit VO (OPT)-induced neurogenesis following brain ischemia. In some behavioral studies, we showed that VO (OPT)-induced neurogenesis accounts for improvement of memory deficits following brain ischemia. These results suggest that intraperitoneal administrations of VO (OPT) stimulate neurogenesis following brain ischemia through PI3K/Akt and ERK activation. Moreover, Akt- and ERK-induced neurogenesis is critical for improvement of memory deficits following brain ischemia.

  20. 新規グルタミン酸配座固定化分子の合成に基づく受容体機能探索子の創製

    渋谷 正俊, 岩渕 好治, 福永 浩司

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 特定領域研究

    Institution: 東北大学

    2006 - 2007

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    アマンタジンを始めとするアダマンタンアミン類がNMDA受容体アンタゴニスト活性にもとづく多様な中枢神経活性を有することから、アダマンタン核上を精密修飾したアダマンタン誘導体が有用な中枢神経活性を示すものと期待し研究を行ってきた。研究開始当初は、アダマンタン核上にグルタミン酸単位を配置したアダマンタン誘導体が有用な中枢神経活性を示すものと期待していたが、前年度の研究において必ずしもアダマンタン核上にグルタミン酸単位を持たなくとも精密修飾アダマンタン類は、中枢神経活性を示すという結果が得られた。この結果を受けて前年度は、アダマンタン誘導体を約40種類合成し、CaMキナーゼIIの活性化を指標として中枢神経活性評価を行ない、中枢神経活性を示唆する約10種の化合物を候補化合物を得た。そこで、本年度の研究では、より生体内条件に近い灌流条件によるアッセイ系を確立し、合成した約40種のアダマンタン誘導体の薬理活性評価を再度行った。その結果、5μMにおいてCaMKIIの自己リン酸化を亢進する化合物ad008,ad013,ad014と抑制する化合物ad003,ad004,ad005が得られた。さらに作用の強かったad013,ad014を用いてラット海馬切片を用いた電気生理学的手法によって詳細に検討を行った結果、これらの化合物は単独でfEPSPを亢進することがわかった。この結果から、これらの化合物はNMDA受容体にアゴニスティックに作用していることが示唆された。Ad013とad014はエナンチオマーであり、作用の違いはほとんどない点でも興味深いが、現在のところ空間的な官能基配置がこれらの化合物では類似しているためであると考えている。

  21. Exploitation of Nitroxyl Radidal-type Organocatalysts for Alcohol Oxidation and their Use in Fine Synthetic Chemistry

    IWABUCHI Yoshiharu, SUGAHARA Tsutomu, SHIBUYA Masatoshi

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2005 - 2007

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    This research project aimed exploitation of synthetic potential of azaadamantane N-oxyl (AZADO)-type nitroxyl radicals as oxidation catalyst for alcohol oxidation and their use in fine synthetic chemistry. We have established the following matters in this research period. (1) The structure-activity correlation of AZADO-type nitroxyl radicals: We synthesized a panel of AZADO-type catalysts and examined their function as oxidation catalyst to clarify the molecular basis of the extremely aggressive nature of AZADO compare to TEMPO. Our experiments have led the conclusion that alleviation of the steric factor near the catalytically active site critically determine the catalytic activity. (2) We have developed several synthetic route to enantiomerically modified AZADOs and have examined their use as enantioselective catalyst for oxidation of secondary alcohols. The results allowed us to develop a tentative mechanistic hypothetic model, which is useful for further development. (3) We have developed a ractical and highly efficient methods for oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated ketones employing oxoxammonium salts. The methods developed are applicable to acyclic substrates as well as medium membered ring substrates and macrocyclic substrates. We have elucidated that counter anion of the oxoxmmonium salt plays crucial roles on this oxidative rearrangement. (4) We have discovered a novel AZADO derivative that made us possible to conduct metal-free, halogen-free aerobic oxidation of aloohols to carbonyl compounds under an ambient temperature.

  22. アダマンタンアミン類の精密構造修飾に基づく高特異的イオンチャネルブロック薬の創製

    岩渕 好治, 森口 茂樹, 澁谷 正俊

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 萌芽研究

    Institution: 東北大学

    2005 - 2006

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    昨年度までの研究から、アダマンタンアミノ酸、アダマンタンアミン類が中枢神経グルタミン酸受容体に対してアンタゴニストおよびアゴニスト活性を惹起することを明らかとした。そこで、本年度はリード化合物としているad001の構造活性相関研究を行うとともに多様なアダマンタン誘導体の中枢神経活性評価を行った。 海馬CaMキナーゼII活性を指標とした神経薬理活性評価法の確立 これまで行ってきた電気生理学的手法は詳細な薬理活性評価を可能とするが、煩雑な操作を要するため多数の化合物の迅速な評価は困難であった。そこで、多様なアダマンタン誘導体の簡便な薬理活性評価法を確立するため検討を行った結果、海馬CaMキナーゼII活性を指標とした方法を確立できた。本法で得た結果は電気生理学的手法で得た結果と良い相関を示した。 アタマンタン誘導体中枢神経活性化合物の探索 上記薬効評価法を用いて、新たに合成した約40種類のアダマンタン誘導体の活性評価を行った。その結果、中枢神経活性を有する約10種類のアダマンタン誘導体を獲得した。 リード化合物ad001の構造活性相関 NMDA受容体アンタゴニスト活性を有するad001のα-アミノ酸部、2つの水酸基が、このものの活性に及ぼす影響を調べる目的で、アミノ酸部の立体化学逆のR配置の誘導体、2つの水酸基をもたないアミノ酸、5位の水酸基を持たないアミノ酸をそれぞれ合成し、薬理活性評価を行った。その結果、アミノ酸部がR配置のアダマンタンアミノ酸はより強い抑制活性を示し、2つの水酸基の有無も活性発現に必須であることが明らかとなった。本年度の研究においてad001の構造のわずかな違いが活性発現に大きく影響することがわか明らかとなった。

  23. キラルアダマンタンアミン類の合成に基づくグルタミン酸受容体機能解明ツールの創製

    岩渕 好治, 福永 浩司, 澁谷 正俊

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 特定領域研究

    Institution: 東北大学

    2005 - 2005

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    当研究室で独自に開発したアダマンタン核不斉修飾法の展開を機軸とし、特異なグルタミン酸受容体作動性を示すアダマンタンアミン類をモチーフとして薬理活性発現が期待される含窒素アダマンタン誘導体を種々合成した。そして、それらの神経薬理学的評価法に基づく構造-活性相関情報を獲得するとともに分子設計へとフィードバックさせて、グルタミン酸受容体機能解明に資する分子ツールの創製を目指した。 先ず、アダマンタンジオールから1工程で得られるビシクロ[3.3.2]ノナノンを起点として、光学活性アダマンタンアミノ酸、アダマンタンアミン類、およびアザアダマンタンに到る基本合成経路を確立した。また、ビシクロ[3.3.2]ノナノン型化合物からの多様なアダマンタンアミン誘導体の合成を可能とするLewis酸触媒Olah型環化手法を確立することができた。 新規に合成したアダマンタン誘導体について、電気生理学的手法を用いてその神経薬理学的評価を行りたところ、アダマンタンアミノ酸Ad001がラット海馬C1領域における長期増強現象を強く抑制することを見出した。本化合物の活性は抗アルツハイマー薬として臨床で用いられているメマンチンを凌駕するものであった。これまでの検討の結果、Ad001はAMPA型グルタミン酸受容体には殆ど作用を及ぼさない一方、NMDA型グルタミン酸受容体に結合してアンタゴニスト活性を発現することが強く示唆されている。現在、Ad001の立体異性体を種々合成して、構造活性相関に関する情報収集を行っている。

  24. Development of a nobel strategy for chemoprevention of colorectal carcinogenesis by using newly synthesized organic compounds derived from natural dietary constituents

    SHIBATA Hiroyuki, IWABUCHI Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (C)

    Institution: TOHOKU UNIVERSITY

    2004 - 2005

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    Curcumin is a dietary constituent of turmeric that is widely used as a spice. Curcumin is a well-studied phytochemical that has a potential to suppress the growth of many cancer cell lines, while that has less toxicity as it is used for daily food. In this study, we have raised the goal to synthesize the new compounds from curcumin bearing the strengthen ability to suppress the growth of tumor cells, but keeping its less toxicity, and to establish a nobel strategy for medication of cancer treatment. The first cycle of the screening, we synthesized a new curcumin analog, GO-035 that have 4 times higher growth suppressive ability. Then we have synthesized over 50 compounds derived from GO-035. Finally two analogs termed GO-Y030 and GO-Y031 have been found out that have 40 times or more growth suppressive abilities against colorectal cancer cell lines. The common characteristic feature of these compounds is a pentanoid having the symmetrical addition of the alkoxy groups to the aromatic rings at both ends. These compounds have a stronger growth suppressive potential against a variety of cancer cell lines derived from stomach, colon, lung, pancreas, ovary, melanoma and so on, compared with chemotherapeutic agents such as cis-platine, 5-FU and irinotecan. The improvements of mechanical aspects of these compounds are the higher potentials to induce a G2/M phase arrest, apoptosis and down-regulation of various oncoproteins including beta-catenin, Ki-Ras, Cyclin-D1, c-Myc and erbb2 at much lower concentration than curcumin. On the other hands, there is no harmful effect on the primary hepatocytes at even 100 micromolar. There is no toxic effect on the mice fed with these conpounds (0.1% (w/w)in daily diet). These features of the compounds is thought to be ideal for not only chemotherapy but also chemoprevention.

  25. Synthetic Studies on Substituted Citrate Natural Products based on the Cinchona Alkaloid-Catalyzed Asymmetric Baylis-Hillman reaction

    IWABUCHI Yoshiharu, HATAKEYAMA Susumi

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (C)

    2001 - 2002

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    We have previously developed a highly enantioselective asymmetric BaylisHillman reaction which allows us to construct a wide variety of (α-methylene-β-hydroxy)esters with highly optical purity (>90% ee). The reaction relies upon the combinatorial use of two important reagents, 1,1,1,3,3,3-hexafluoroisopropyl acrylate as an activated alkene and (3R, 8K,,9S)-10,11-dihydro-3,9-epoxy-6'-hydroxy-cinchonane as a chiral, nucleophilic amine catalyst. In this research program, we have established the synthetic utility of the reaction system in a practical sense, by demonstrating its applicability to the crucial step in total syntheses of biologically active natural products, including a potent immunosuppressant amino acid, (-)-mycestericin E, and a novel proteasome inhibitor epopromycin B. The reaction was found to be applicable to α-keto ester-type substrates to furnish the corresponding α-methylene-β-alkoxycatbonyl-β-hydroxy)esters in good chemical yield with modest enantioselectivity. These reaction products should serve as useful synthons for the preparation of a series of substituted citratetype compounds.

  26. Synthesis of structurally unique natural products having glutamate receptor agonist and antagonist activities

    HATAKEYAMA Susumi, IWABUCHI Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Nagasaki University

    2001 - 2002

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    The compounds that interact with glutamate receptors are in high demand in order to investigate the relationship between glutamate receptors and brain diseases. These compounds are also useful for designing a new type of glutamate receptor antagonist which may have therapeutic value as a neuroprotective agent. In this research, we focused on dysiherbaine, a glutamate receptor agonist isolated from Dysidea herbacea, and kaitocephalin, a glutamate receptor antagonist isolated from Eupenicillium shearii PF1191 strain, and aimed to develop efficient methods for the syntheses of these compounds. For dysiherbaine, we have developed an efficient method for the preparation of the key intermediate starting with D-glucose based on highly stereoselective Hosomi-Sakurai reaction to attach the side chain to the pyrane ring and palladium catalyzed cross-coupling reaction of the functionalized enol triflate and the organozinc reagent derived from L-iodoalanine to install the glutamic acid moiety. For kaitocephalin, we examined 1, 3-butadienylation of the Garner aldehyde derived from L-serine. When the Garner aldehyde was reacted with 2, 3-butadienyltrichlorostannane, prepared in site from 1, 3-butadien-2-yltributylstananne and SnCl_4, the addition reaction proceeded with perfect anti-selectivity to give the compound convertible to kaitocephalin.

  27. 脳神経系の分子レベルでの機能解明を目指す精密有機合成化学的アプローチ

    岩渕 好治, 畑山 範

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 特定領域研究(A)

    Institution: 長崎大学

    1999 - 2000

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    1996年にミクロネシア産海綿(Dysidea herbacea)から単離された新規異常アミノ酸、Dysiherbaine(DH)は、これまで知られるなかで最も強力な神経興奮毒性を示し、その特異な構造と機能の相関に関する知見は、グルタミン酸受容体サブタイプの分類やその脳内における分布と脳疾患との関連性、グルタミン酸受容体のアンタゴニストの分子設計など、神経薬理学の分野で今後幅広く活用されることが期待される。我々は、DHの合成研究の途上で、DHの構造的特徴を含む天然物Lycoperdic Acid(LA)を文献上に見いだし、このものをDHの特異性評価の格好の対照化合物と位置付け、種々のLA誘導体の活性評価を通じてDHの特異な生物活性発現の構造的要因の特定を目指した。LAは1978年、ヨーロッパ産のキノコ(Lycoperdon perlatum)から単離されたアミノ酸であり、その化学構造からグルタミン酸様のアゴニスト活性を示すことが予想されるが、薬理学的な性質は全く知られておらず、この点も興味が持たれた。 リガンド結合実験の結果、(1)DHおよびLAはカイニン酸型サブタイプ選択的リガンドであり、(2)その結合活性は4位立体化学および環状構造が決定的な因子となっていることが判明した。また、DH,LAとdeoxo-LAとの活性比較から、(3)7位周辺の極性基がリガンド結合活性に極めて重要な役割を果たしていることが示唆された。現在、これらの個体レベルでの活性評価の準備を進めている。

  28. 新規抗マラリア剤の開発を目指すフェブリフジン類アルカロイドの合成研究

    畑山 範, 岩渕 好治

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 特定領域研究(A)

    Institution: 長崎大学

    1999 - 1999

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    最近、漢薬・常山の主要植物ジョウザンアジサイに含まれるフェブリフジンから導かれる誘導体がマラリア原虫に対して高い選択性をもって抗マラリア活性を示すことが明らかとされ、フェブリフジンが抗マラリア剤開発のリードとしてあらためて注目を集めている。この様な背景をうけて、我々は、フェブリフジンはもとより多様な類縁体の量的供給を可能にする実用的合成法を確立することを目的とし、本課題研究を行った。その結果、フェブリフジンを三つのパーツに分けて合成し、それらをカップリングさせる三成分連結法に基づくコンバージェント合成法を開発し、フェブリフジンのエナンチオ選択的合成に成功した。すなわち、(S)-4-4(t-ブチルジフェニルシリル)オキシ-5-ヘキセニルメシラートをオゾン分解後アリルアルコール共存下ヒドロキシルアミン塩酸塩で処理すると、ニトロンの形成と1,3-双極付加が一挙に進行し付加体が収率良く生成することを見いだし、このものに数段階を経て4-キナゾリノールを連結させ(+)-フェブリフジンの合成に成功した。さらに、上記合成法に従い4種の誘導体を合成し、抗マラリア活性試験に供した。このことによって、本合成法が、誘導体合成にも柔軟な合成法であることを示すことができた。

  29. 触媒的不斉Baylis-Hillman反応の開発とその活用に関する研究

    岩渕 好治

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 奨励研究(A)

    Institution: 長崎大学

    1998 - 1999

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    触媒量の3級アミン存在下、アクリル酸エステルがアルデヒドと縮合してβ-ヒドロキシ-α-メチレンエステルを与えるBaylis-Hillman反応は、3級アミンが求核触媒として作用するユニークな反応様式とその合成化学的有用性から注目を集めている。本反応は上述の試薬の混合物を室温下放置するだけで進行するが、反応の終結には数週間から一カ月もの長時間を要するという問題点を含んでいる。しかし、基質および反応系のいずれにおいても極めて単純であることから、反応時間を短縮するとともに、高い光学純度を有する生成物を与える触媒を開発できれば極めて魅力的な不斉合成法が誕生することになる。 我々は、水素結合の関与を機軸とする協同的多点相互作用による反応加速と不斉発現を期待して、水酸基を有するキラル3級アミンを合成し、それらの不斉触媒としての反応性を精査した。そしてごく最近、最高99%ee以上の光学純度で生成物が得られる触媒と反応系を見い出し、これより世界で初めて、高い一般性を有する触媒的不斉Baylis-Hillman反応を開発することに成功した(J.Am.Chem.Soc.,1999,121,10219-10220)。

  30. Exploitation of an Efficient and Practical Method for the Synthesis of Active Vitamin D_3 Derivatives

    HATAKEYAMA Susumi, KUBODERA Noboru, IWABUCHI Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Nagasaki University

    1995 - 1997

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    Since 1alpha, 25-dihydroxyvitamin D_3 was found to play an important role in the modulation of cell proliferation and differentiation as well as in the maintenance of calcium homeostasis, a great deal of attention has been paid to the synthesis of its structural analogs to separate and improve its each inherent biological activities. In this research, we aimed to develop efficient and practical synthetic methods useful for the convergent synthesis of various vitamin D_3 analogs. Because a convergent approach involving coupling of a A-ring fragment and a C/D-ring fragment is much more beneficial than an approach based on photolysis of cholesta-5,7-diene derivatives due to easy access to its unnatural variants. Firstly, we have developed an efficient method for the preparation of a C/D-ring fragment for 20-epi-22-oxavitamin D_3 analogs based on TMSOTf catalyzed reductive etherification of a ketone with an alkoxytrimethylsilane in the presence of Et_3SiH.Secondly, we have developed a concise method for the synthesis of A-ring fragments on the basis of the new strategy which centers around palladium (0) catalyzed intramolecular Heck type of reaction of the enol triflate derived from a beta-keto ester. Thirdly, we have succeeded in the first convergent synthesis of 1alpha, 25-dihydroxy-2beta-(3-hydroxypropoxy) vitamin D_3 (ED-71) through coupling of the corresponding A-ring fragment and the C/D-ring fragment.

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