Details of the Researcher

PHOTO

Shota Nagasawa
Section
Graduate School of Pharmaceutical Sciences
Job title
Assistant Professor
Degree

  • 博士（薬科学）（東北大学）

  • 修士（薬科学）（東北大学）

Research History 4

  • 2019/04 - Present
    Tohoku University　Graduate School of Pharmaceutical Sciences

  • 2017/06 - 2019/03
    University of California, Berkeley

  • 2017/04 - 2017/05
    Tohoku University　Graduate School of Pharmaceutical Sciences

  • 2014/04 - 2017/03
    日本学術振興会　特別研究員（DC1)

Education 1

  • Tohoku University　Graduate School of Pharmaceutical Sciences　Division of Molecular Pharmaceutical Chemistry

    2012/04 - 2017/03

Professional Memberships 3

  • THE JAPANESE SOCIETY FOR PROCESS CHEMISTRY

  • THE SOCIETY OF SYNTHETIC ORGANIC CHEMISTRY, JAPAN

  • THE PHARMACEUTICAL SOCIETY OF JAPAN

Research Interests 1

  • 有機合成化学

Research Areas 1

  • Life sciences / Pharmaceuticals - chemistry and drug development /

Papers 26

  1. Strategy for C−H Functionalization of Cubanes: From Stoichiometric Reaction to Catalytic Methodology

    Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi

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

    Publisher: Wiley

    DOI： 10.1002/ejoc.202401055 　

    ISSN： 1434-193X

    eISSN： 1099-0690

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    Abstract We summarized a strategy for C−H functionalization of cubanes, highlighting recent progress in the field. Cubane, known as a bioisostere of benzene ring, and its functionalization hold significant potential for future drug development. However, owing to its highly strained and thermodynamically unstable nature, the methodologies are limited and their precise and diverse functionalization is challenging in current organic chemistry. In this Concept, we categorized and explained these methodologies, which represents a majority of current cubane C−H functionalization. In addition, we discussed recent advancements in catalytic C−H functionalization methods, demonstrating their potential to address these challenges effectively.

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

    Shota Nagasawa, Yoshiharu Iwabuchi

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

    Publisher: Georg Thieme Verlag KG

    DOI： 10.1055/a-2360-8218 　

    ISSN： 0039-7881

    eISSN： 1437-210X

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    Abstract Recently, many saturated bioisosteres of the benzene ring have been developed, and their applications in drug development have been evaluated. Most of these bioisosteres are caged hydrocarbons, which have rigid skeletons and three-dimensional spaces. Recent efforts to synthesize these caged hydrocarbons have enabled access to multi-functionalized congeners that are expected to be (bio)isosteres of multi-functionalized benzenes. This short review summarizes recently reported methods for obtaining multi-functionalized (typically more than disubstituted) caged hydrocarbons. 1 Introduction 2 Proposed Structures of Caged Hydrocarbons as Saturated (Bio)isosteres of the Benzene Ring: A Brief Summary 3 Access to Multi-functionalized Caged Hydrocarbons: De Novo Synthetic Approaches 3.1 Bicyclo[1.1.1]pentanes (BCPs) 3.2 Bicyclo[2.1.1]hexanes (BCHs) 3.3 Bicyclo[3.1.1]heptanes (BCHeps) 3.4 Others 4 Access to Multi-functionalized Caged Hydrocarbons: C–H Functionalization 5 Conclusion

  3. Controlled Aerobic Oxidative Dimerization of Hydroxystilbenoids by Chromium Catalysis

    Shota Nagasawa, Yudai Itagaki, Yusuke Sasano, Yoshiharu Iwabuchi

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

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.orglett.4c00839 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  4. Biological Evaluation of Isosteric Applicability of 1,3-Substituted Cuneanes as m-Substituted Benzenes Enabled by Selective Isomerization of 1,4-Substituted Cubanes. International-journal

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

    Chemistry (Weinheim an der Bergstrasse, Germany)　30　(11)　e202303548　2024/02/21

    DOI： 10.1002/chem.202303548 　

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    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.

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

    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

  6. C–H Alkylation of Cubanes via Catalytic Generation of Cubyl Radicals

    Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi

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

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.orglett.3c04019 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  7. Asymmetric Total Synthesis of Cytotrienin A: Late-stage Installation of C11 Side Chain onto the Macrolactam Scaffold. International-journal

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

    Angewandte Chemie (International ed. in English)　e202303140　2023/05/22

    DOI： 10.1002/anie.202303140 　

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    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 hydroxyl group via 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.

  8. 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

    Publisher: Wiley

    DOI： 10.1002/ajoc.202300031 　

    ISSN： 2193-5807

    eISSN： 2193-5815

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    Abstract Concise synthesis and structure‐activity relationships study of 4‐substituted 2‐azaadamantane N‐oxyls reveals that 4‐chloro‐2‐azaadamantane N‐oxyl (4‐Cl‐AZADO) is an efficient organocatalyst toward the aerobic oxidation of alcohols in the presence of NOx as a co‐catalyst. The organocatalyst was easily synthesized from 2‐adamantanone in five steps, and it showed high activity compared with many previously reported nitroxyl radical catalysts.

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

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

    CHEMICAL COMMUNICATIONS　59　(9)　1237-1240　2023/01

    DOI： 10.1039/d2cc06301h 　

    ISSN： 1359-7345

    eISSN： 1364-548X

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

    Daigo Ninomiya, Shota Nagasawa, Yoshiharu Iwabuchi

    ORGANIC LETTERS　24　(41)　7572-7576　2022/10

    DOI： 10.1021/acs.orglett.2c02960 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  11. 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

    Publisher: American Chemical Society ({ACS})

    DOI： 10.1021/acs.joc.1c01760 　

    ISSN： 0022-3263

    eISSN： 1520-6904

  12. Design, Synthesis, and Antifungal Activity of 16,17-Dihydroheronamide C and ent-Heronamide C

    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　2021/12/03

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.joc.1c01761 　

    ISSN： 0022-3263

    eISSN： 1520-6904

  13. 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

    Publisher: American Chemical Society ({ACS})

    DOI： 10.1021/acs.orglett.1c03144 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  14. 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

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

    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

  16. Enantiospecific Entry to a Common Decalin Intermediate for the Syntheses of Highly Oxygenated Terpenoids Peer-reviewed

    Shota Nagasawa, Kerry E. Jones, Richmond Sarpong

    The Journal of Organic Chemistry　84　(18)　12209-12215　2019/09/20

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.joc.9b01937 　

    ISSN： 0022-3263

    eISSN： 1520-6904

  17. Rearrangement of Hydroxylated Pinene Derivatives to Fenchone-Type Frameworks: Computational Evidence for Dynamically-Controlled Selectivity Peer-reviewed

    Blümel, M, Nagasawa, S, Blackford, K, Hare, S. R, Tantillo, D. J, Sarpong, R

    J. Am. Chem. Soc.　140　9291　2018

    DOI： 10.1021/jacs.8b05804 　

  18. 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

    DOI： 10.1021/acs.orglett.8b02528 　

    ISSN： 1523-7060

    eISSN： 1523-7052

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

    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

  20. 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

  21. 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

  22. 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

  23. 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

  24. Highly Chemoselective Aerobic Oxidation of Amino Alcohols into Amino Carbonyl Compounds Peer-reviewed

    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

  25. 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

  26. 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

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Misc. 9

  1. Photosensitized Singlet Oxygen-supported Alcohol Oxidation Mediated by Nitroxyl Radical Catalyst

    西嶋政樹, 長澤翔太, 笹野裕介, 荒木保幸, 岩渕好治, 和田健彦

    日本化学会春季年会講演予稿集(Web)　103rd　2023

  2. THE UTILITY OF OXOAMMONIUM SPECIES IN ORGANIC SYNTHESIS: BEYOND ALCOHOL OXIDATION Peer-reviewed

    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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

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Research Projects 5

  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. 遷移金属触媒的C-H官能基化を基盤とするキュバン修飾法の開発とその医薬化学的応用

    長澤 翔太

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 若手研究

    Institution: 東北大学

    2021/04/01 - 2023/03/31

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    前年度までに萌芽的成果を得ていたキュバンのCーHアセトキシ化反応について，その最適化検討を行い，基質適用性の検討を行った．また，得られたアセトキシ化キュバンについて，各種官能基変換を行うことで医薬品ならびに芳香族複素環のキュバンアナログの合成に成功した．これらの成果についてまとめて学術雑誌に投稿し，採択された (Organic Letters, 2021, 23, 8717)．本論文はSupplementary Cover Art にも採択された． 一方で，上記結果を踏まえ研究実施計画に記した内容について，以下の結果を得た． 1．キュバンC-H結合の効率的な直截的転換を可能とする配向基の探索を行った．オキシム型配向基を種々検討したが，先述した論文記載のものを上回る効率性を有する配向基を見出すことはできなかった．そこで，オキシム型からの脱却を志向し，他の配向基によるC-H官能基化に実績のある置換基を，先に見出した条件を用いて再度検討した．その結果，特定のアミド型配向基において高い効率性で先述のアセトキシ化反応が進行することを見出した．この萌芽的結果を元に，現在配向基の最適化検討を進めている． 2．分子内C-H官能基化反応によるキュバン縮環型化合物の合成検討を行った．ロジウム等を用いる各種C-H挿入反応や，C-H活性化を経る官能基化を試みたものの，所望の官能基化キュバンを得ることはできなかった．この結果，並びに研究代表者の過去の知見から，これら分子内反応による官能基化はキュバンの特殊な構造的特徴に由来して困難であると考え，新たな分子間反応に基づくC-H官能基化法を探索することとして検討を行った．その結果，新たな分子間C-H官能基化法に基づくキュバン官能基化手法を見出すに至った．

  3. Radical-initiated C-H functionalization of cubane for medicinal chemistry

    Nagasawa Shota

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research Grant-in-Aid for Research Activity start-up

    Category: Grant-in-Aid for Research Activity start-up

    Institution: Tohoku University

    2019/08 - 2021/03

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    Unfortunately, an appropriate directing groups and conditions for radical-initiated C-H functionalization have not been found. On the other hand, introduction of an acetoxy group into cubane skeleton have been achieved by applying reaction conditions for transition-metal catalyzed C-H functionalization. Furthermore, the obtained acetoxylated compound could be converted into a cubane analog of pharmaceutically important aromatics. Preparation of manuscript including these result is underway.

  4. 抗腫瘍活性天然物 Taxagifine およびその誘導体の合成研究 Competitive

    Offer Organization: 内藤記念科学振興財団

    System: 海外留学助成金

    2017/06 - 2018/05

  5. アザアダマンタン型オキソアンモニウム塩を触媒とするオレ フィン類空気酸化反応の開発 Competitive

    Offer Organization: 日本学術振興会

    System: 特別研究員奨励費

    2014/04 - 2017/03