Details of the Researcher

PHOTO

Naoki Mori
Section
Graduate School of Science
Job title
Senior Assistant Professor
Degree

  • Ph.D. (The University of Tokyo)

e-Rad No.
60463882

Research History 6

  • 2020/01 - Present
    東北大学大学院理学研究科化学専攻　講師

  • 2019/04 - 2019/12
    公益財団法人乙卯研究所　研究員

  • 2018/05 - 2019/03
    東京大学大学院農学生命科学研究科　特任講師

  • 2008/05 - 2018/04
    東京大学大学院農学生命科学研究科　助教

  • 2007/06 - 2008/04
    東京大学大学院農学生命科学研究科　特任助教

  • 2007/04 - 2007/05
    東京大学大学院農学生命科学研究科　リサーチフェロー

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Education 3

  • 東京大学大学院農学生命科学研究科応用生命化学専攻博士課程

    2004/04 - 2007/03

  • 東京大学大学院農学生命科学研究科応用生命化学専攻修士課程

    2002/04 - 2004/03

  • 東京大学農学部生物生産科学課程生命化学専修

    1998/04 - 2002/03

Awards 1

  1. 農芸化学奨励賞

    2017/03

Papers 45

  1. Enantioselective Synthesis of α‐Trifluoromethyl tert‐Alcohols and Amines via Organocatalyst‐Mediated Aldol and Mannich Reactions Peer-reviewed

    Yujiro Hayashi, Hinata Odaira, Masashi Tomikawa, Naoki Mori, Tohru Taniguchi, Kenji Monde

    Asian Journal of Organic Chemistry　14　(4)　2025/02/06

    Publisher: Wiley

    DOI： 10.1002/ajoc.202500035 　

    ISSN： 2193-5807

    eISSN： 2193-5815

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    Abstract The asymmetric aldol reaction of ethyl trifluoropyruvate with aldehydes was developed using diarylprolinol as a catalyst, affording α‐trifluoromethyl‐substituted tertiary alcohols with high enantioselectivity. Similarly, the asymmetric Mannich reaction of aldehydes with an imine derived from ethyl trifluoropyruvate was developed using diphenylprolinol silyl ether in combination with an acid, yielding α‐trifluoromethyl‐substituted tertiary amines. The absolute and relative configurations of the products were determined by vibrational circular dichroism (VCD).

  2. Synthesis of Consecutive All-Carbon Quaternary Centers via Three-Step Reactions Peer-reviewed

    Xiaolei Han, Huazhuo Ban, Naoki Mori, Yujiro Hayashi

    Organic Letters　26　(50)　10840-10845　2024/12/09

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.orglett.4c03945 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  3. Identification of olfactory alarm substances in zebrafish Peer-reviewed

    Miwa Masuda, Sayoko Ihara, Naoki Mori, Tetsuya Koide, Nobuhiko Miyasaka, Noriko Wakisaka, Keiichi Yoshikawa, Hidenori Watanabe, Kazushige Touhara, Yoshihiro Yoshihara

    Current Biology　34　(7)　1377-1389　2024/04

    Publisher: Elsevier BV

    DOI： 10.1016/j.cub.2024.02.003 　

    ISSN： 0960-9822

  4. Organocatalyst-mediated asymmetric one-pot/two domino/three-component coupling reactions for the synthesis of trans-hydrindanes Peer-reviewed

    Naoki Mori, Toshiki Tachibana, Nariyoshi Umekubo, Yujiro Hayashi

    Chemical Science　15　(15)　5627-5632　2024/03

    Publisher: Royal Society of Chemistry (RSC)

    DOI： 10.1039/d4sc00193a 　

    ISSN： 2041-6520

    eISSN： 2041-6539

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    Highly substituted trans-hydrindanes were synthesized by the three-component coupling reactions of 1,3-diethyl 2-(2-oxopropylidene)propanedioate and two different α,β-unsaturated aldehydes catalyzed by diphenylprolinol silyl ether.

  5. Oxidative Synthesis of α‐Nitroketones from α‐Substituted Malononitrile and Nitromethane Using Molecular Oxygen without Condensation Reagents Peer-reviewed

    Yujiro Hayashi, Emanuele Cocco, Hinata Odaira, Hiroaki Matoba, Naoki Mori

    European Journal of Organic Chemistry　27　(6)　e202300964　2024/01/15

    Publisher: Wiley

    DOI： 10.1002/ejoc.202300964 　

    ISSN： 1434-193X

    eISSN： 1099-0690

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    Abstract We developed an oxidative synthetic method for α‐nitroketones from α‐substituted malononitriles and nitromethane under molecular oxygen. Only base and molecular oxygen are necessary without condensation reagents; this is an environmentally benign synthesis.

  6. Bis(2-ethylhexyl)amine as an Effective Organocatalyst for the Racemic Reactions of α,β-Unsaturated Aldehydes Involving an Iminium Ion Peer-reviewed

    Yujiro Hayashi, Xiaolei Han, Naoki Mori

    Synlett　34　(20)　2423-2428　2023/09/21

    Publisher: Georg Thieme Verlag KG

    DOI： 10.1055/a-2179-5916 　

    ISSN： 0936-5214

    eISSN： 1437-2096

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    Abstract Bis(2-ethylhexyl)amine is shown to be a suitable organocatalyst to prepare racemic compounds in the reactions of α,β-unsaturated aldehydes involving an iminium ion, whereas diphenylprolinol silyl ether is a well-known chiral organocatalyst for the asymmetric versions of the same reactions. The generality and limitations of bis(2-ethylhexyl)amine are disclosed.

  7. Secondary Amine‐Mediated Domino Reaction for the Synthesis of Substituted Quinolines from Dicyanoalkenes and Enynals Peer-reviewed

    Yujiro Hayashi, Xiaolei Han, Naoki Mori

    Chemistry – A European Journal　29　(40)　e202301093　2023/05/31

    Publisher: Wiley

    DOI： 10.1002/chem.202301093 　

    ISSN： 0947-6539

    eISSN： 1521-3765

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    Abstract Substituted quinolines, tricyclic and tetracyclic molecules with a quinoline moiety are synthesized by a domino reaction from dicyanoalkenes and 3‐aryl‐pent‐2‐en‐4‐ynals in one pot. We established two methods: one is catalyzed by chiral diphenylprolinol silyl ether, and the other is catalyzed by di(2‐ethyl)hexylamine, in combination with p‐nitrophenol. A wide variety of dicyanoalkenes can be employed. As the catalysts are secondary amines, and water is the only by‐product, this is an environmentally benign synthetic method for the preparation of substituted quinolines.

  8. Diphenylprolinol Silyl Ether Catalyzed Asymmetric Formal Carbo [3+3] Cycloaddition Reaction of Isopropylidenemalononitrile and α,β‐Unsaturated Aldehyde Peer-reviewed

    Nariyoshi Umekubo, Xiaolei Han, Naoki Mori, Yujiro Hayashi

    European Journal of Organic Chemistry　2022　(26)　e202200603　2022/07/14

    Publisher: Wiley

    DOI： 10.1002/ejoc.202200603 　

    ISSN： 1434-193X

    eISSN： 1099-0690

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    Abstract Enantioselective formal carbo [3+3] cycloaddition reaction of isopropylidenemalononitrile (1) and α,β‐unsaturated aldehyde, catalyzed by diphenylprolinol silyl ether, was developed. The reaction is a domino Michael/aldol‐type reaction, followed by Al2O3‐mediated dehydration to afford 5‐substituted cyclohexene derivatives possessing a methylene‐malononitrile moiety, with excellent enantioselectivity.

  9. Asymmetric Michael Reaction of Malononitrile and α,β-Unsaturated Aldehydes Catalyzed by Diarylprolinol Silyl Ether Peer-reviewed

    Yujiro Hayashi, Yutaro Hatano, Naoki Mori

    Synlett　33　1831-1836　2022/06/09

    Publisher: Georg Thieme Verlag KG

    DOI： 10.1055/a-1846-5007 　

    ISSN： 0936-5214

    eISSN： 1437-2096

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    Abstract An asymmetric Michael reaction of malononitrile and α,β-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether was developed. Michael products were obtained in good yields and with excellent enantioselectivities without the formation of overreaction products. As a malononitrile moiety can be transformed into an alkoxy or amino carbonyl moiety by oxidative transformation, α-chiral esters or amides with all-carbon quaternary centers can be synthesized with excellent enantioselectivities.

  10. Diarylprolinol with Trifluoromethyl Substituents and Diphenylprolinol‐Derived Perfluoroalkanesulfonamide as Organocatalysts in the Cross‐Aldol Reaction of Aldehydes Invited Peer-reviewed

    Yujiro Hayashi, Masashi Tomikawa, Naoki Mori

    Advanced Synthesis & Catalysis　364　(19)　3424-3431　2022/05/16

    Publisher: Wiley

    DOI： 10.1002/adsc.202200266 　

    ISSN： 1615-4150

    eISSN： 1615-4169

  11. Asymmetric Synthesis of Pentasubstituted Cyclohexanes through Diphenylprolinol Silyl Ether Mediated Domino Michael/Michael Reaction Peer-reviewed

    Amaechi Shedrack Odoh, Louise Aidanpää, Nariyoshi Umekubo, Hiroaki Matoba, Naoki Mori, Yujiro Hayashi

    European Journal of Organic Chemistry　2021　(48)　6670-6673　2021/12/28

    Publisher: Wiley

    DOI： 10.1002/ejoc.202101106 　

    ISSN： 1434-193X

    eISSN： 1099-0690

  12. Three-Pot Synthesis of Chiral Anti-1,3-diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Epoxidation and Reductive Opening of the Epoxide Peer-reviewed

    Yujiro Hayashi, Masashi Tomikawa, Naoki Mori

    Organic Letters　23　(15)　5896-5900　2021/08/06

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.orglett.1c01986 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  13. Formal Synthesis of Pseudolaric Acid B Peer-reviewed

    Naoki Mori

    Synlett　31　(09)　907-910　2020/06

    Publisher: Georg Thieme Verlag KG

    DOI： 10.1055/s-0039-1690829 　

    ISSN： 0936-5214

    eISSN： 1437-2096

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    A formal synthesis of pseudolaric acid B, a diterpene isolated from the root bark of Pseudolarix kaempferi Gordon (Pinaceae), to Trost’s synthetic intermediate was achieved in 17 steps from a known ketone. Key features of this synthesis include a Claisen rearrangement and iodoetherification to construct quaternary stereocenters and ring-closing metathesis to form the seven-membered ring.

  14. Studies toward the enantioselective synthesis of neurymenolide A: Construction of the macrocyclic core via Claisen rearrangement Peer-reviewed

    Masahiro Masuda, Natsuki Sakurai, Yusuke Ogura, Tetsuji Murase, Tsuneomi Kawasaki, Shohei Aiba, Naoki Mori, Hidenori Watanabe, Hirosato Takikawa

    Tetrahedron Letters　61　(18)　151825-151825　2020/04

    DOI： 10.1016/j.tetlet.2020.151825 　

    ISSN： 0040-4039

  15. A suicide enzyme catalyzes multiple reactions for biotin biosynthesis in cyanobacteria International-journal Peer-reviewed

    Kei Sakaki, Keita Ohishi, Tetsu Shimizu, Ikki Kobayashi, Naoki Mori, Kenichi Matsuda, Takeo Tomita, Hidenori Watanabe, Kan Tanaka, Tomohisa Kuzuyama, Makoto Nishiyama

    Nature Chemical Biology　16　(4)　415-422　2020/04

    Publisher: Springer Science and Business Media LLC

    DOI： 10.1038/s41589-019-0461-9 　

    ISSN： 1552-4450

    eISSN： 1552-4469

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    In biotin biosynthesis, the conversion of pimeloyl intermediates to biotin is catalyzed by a universal set of four enzymes: BioF, BioA, BioD and BioB. We found that the gene homologous to bioA, the product of which is involved in the conversion of 8-amino-7-oxononanoate (AON) to 7,8-diaminononanoate (DAN), is missing in the genome of the cyanobacterium Synechocystis sp. PCC 6803. We provide structural and biochemical evidence showing that a novel dehydrogenase, BioU, is involved in biotin biosynthesis and functionally replaces BioA. This enzyme catalyzes three reactions: formation of covalent linkage with AON to yield a BioU-DAN conjugate at the ε-amino group of Lys124 of BioU using NAD(P)H, carboxylation of the conjugate to form BioU-DAN-carbamic acid, and release of DAN-carbamic acid using NAD(P)+. In this biosynthetic pathway, BioU is a suicide enzyme that loses the Lys124 amino group after a single round of reaction.

  16. Metachromins X and Y from a marine sponge Spongia sp. and their effects on cell cycle progression International-journal Peer-reviewed

    Yuki Hitora, Kentaro Takada, Yuji Ise, Sau Pinn Woo, Seiya Inoue, Naoki Mori, Hirosato Takikawa, Shohei Nakamukai, Shigeru Okada, Shigeki Matsunaga

    Bioorganic & Medicinal Chemistry　28　(2)　115233-115233　2020/01

    Publisher: Elsevier BV

    DOI： 10.1016/j.bmc.2019.115233 　

    ISSN： 0968-0896

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    New sesquiterpene quinones, metachromins X (1) and Y (2), together with the known metachromins C (3), J (4), and T (5), were isolated as inhibitors of cell cycle progression in the HeLa/Fucci2 cells. The structure of 1 was assigned by spectroscopic data and confirmed by a total synthesis. The planar structure of 2 was determined by interpretation of spectroscopic data, whereas its absolute configuration was analyzed by a combination of chiral HPLC and CD spectroscopy. Metachromins X (1) and C (3) arrested the cell cycle progression of HeLa/Fucci2 cells at S/G2/M phase.

  17. First enantioselective synthesis of salinipostin A, a marine cyclic enol-phosphotriester isolated from Salinispora sp Peer-reviewed

    Hironori Okamura, Takanobu Fujioka, Naoki Mori, Tohru Taniguchi, Kenji Monde, Hidenori Watanabe, Hirosato Takikawa

    Tetrahedron Letters　60　(32)　150917-150917　2019/08

    DOI： 10.1016/j.tetlet.2019.07.008 　

    ISSN： 0040-4039

  18. Concise synthesis of (±)-litseaones A and B International-journal Peer-reviewed

    Hideaki Kageji, Naoki Mori, Hirosato Takikawa, Hidenori Watanabe

    Bioscience, Biotechnology, and Biochemistry　83　(5)　810-812　2019/05/04

    Publisher: Informa UK Limited

    DOI： 10.1080/09168451.2018.1562881 　

    ISSN： 0916-8451

    eISSN： 1347-6947

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    A concise synthesis of litseaones A and B, which were isolated from the stem barks of Litsea rubescens and L. pedunculata, is described in this study. Litseaone A was synthesized in just three steps from a known phloroglucinol derivative. The direct conversion of litseaone A into litseaone B was also achieved.

  19. Synthesis-guided structure revision of the monoterpene alcohol isolated from Mentha haplocalyx International-journal Peer-reviewed

    Shunsuke Konishi, Naoki Mori, Hirosato Takikawa, Hidenori Watanabe

    Bioscience, Biotechnology, and Biochemistry　83　(3)　391-399　2019/03/04

    Publisher: Informa UK Limited

    DOI： 10.1080/09168451.2018.1549936 　

    ISSN： 0916-8451

    eISSN： 1347-6947

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    The monoterpene isolated from Mentha haplocalyx, 3,3,5-trimethyl-2-oxabicyclo[2.2.2]oct-5-en-4-ol, was synthesized according to its proposed structure. However, the NMR data of the synthetic sample were not in agreement with those reported for the natural product. After considerable efforts, the genuine structure was confirmed as (1R*,2R*)-4-(1'-hydroxy-1'-methylethyl)-1-methylycyclohex-3-ene-1,2-diol.

  20. First enantioselective synthesis of exiguamide, a nitrogen-containing spirocyclic sesquiterpene isolated from the marine sponge Geodia exigua Peer-reviewed

    Shunsuke Konishi, Yuki Mitani, Naoki Mori, Hirosato Takikawa, Hidenori Watanabe

    Tetrahedron　75　(5)　652-657　2019/02

    DOI： 10.1016/j.tet.2018.12.046 　

    ISSN： 0040-4020

  21. Novel indole and benzothiophene ring derivatives showing differential modulatory activity against human epithelial sodium channel subunits, ENaC and Peer-reviewed

    Yoichi Kasahara, Takanobu Sakurai, Ryusei Matsuda, Masataka Narukawa, Akihito Yasuoka, Naoki Mori, Hidenori Watanabe, Takayoshi Okabe, Hirotatsu Kojima, Keiko Abe, Takumi Misaka, Tomiko Asakura

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY　83　(2)　243-250　2019

    DOI： 10.1080/09168451.2018.1533802 　

    ISSN： 0916-8451

    eISSN： 1347-6947

  22. Synthesis of both enantiomers of conosilane A Peer-reviewed

    Hironori Okamura, Naoki Mori, Hidenori Watanabe, Hirosato Takikawa

    Tetrahedron Letters　59　(50)　4397-4400　2018/12

    DOI： 10.1016/j.tetlet.2018.10.066 　

    ISSN： 0040-4039

  23. Synthesis and structure revision of litseaone A Peer-reviewed

    Hideaki Kageji, Naoki Mori, Hirosato Takikawa, Hidenori Watanabe

    Tetrahedron　74　(49)　7074-7081　2018/12

    DOI： 10.1016/j.tet.2018.10.041 　

    ISSN： 0040-4020

    eISSN： 1464-5416

  24. First synthesis of (±)-myristicyclin A International-journal Peer-reviewed

    Shinichiro Kubo, Naoki Mori, Hidenori Watanabe, Hirosato Takikawa

    Bioscience, Biotechnology, and Biochemistry　82　(11)　1867-1870　2018/11/02

    Publisher: Informa UK Limited

    DOI： 10.1080/09168451.2018.1495553 　

    ISSN： 0916-8451

    eISSN： 1347-6947

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    The first synthesis of myristicyclin A, which was isolated from the Papua New Guinean plant Horsfieldia spicata, is described. The synthesis features acid-mediated hydroarylation reaction to form a dihydrocoumarin moiety, construction of the 2,8-dioxabicyclo[3.3.1]nonane skeleton under acidic conditions, and regioselective Friedel-Crafts acylation at a later stage.

  25. First synthesis of (±)-pseudohygrophorone A12, an anti-fungal cyclohexenone derivative isolated from Hygrophorus abieticola Peer-reviewed

    Yuzuki Yamamoto, Naoki Mori, Hidenori Watanabe, Hirosato Takikawa

    Tetrahedron Letters　59　(38)　3503-3505　2018/09

    DOI： 10.1016/j.tetlet.2018.08.027 　

    ISSN： 0040-4039

  26. A novel synthesis of (−)-callicarpenal Peer-reviewed

    Daichi Oguro, Naoki Mori, Hirosato Takikawa, Hidenori Watanabe

    Tetrahedron　74　(39)　5745-5751　2018/09

    DOI： 10.1016/j.tet.2018.08.012 　

    ISSN： 0040-4020

  27. Enantioselective Total Synthesis of (+)-Anthecularin Peer-reviewed

    Yusuke Ogura, Shoko Okada, Naoki Mori, Ken Ishigami, Hidenori Watanabe

    Organic Letters　20　(13)　3888-3891　2018/07/06

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.orglett.8b01467 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  28. Synthetic studies on pseudolaric acid B: Construction of the trans-fused [5–7] ring system via Dieckmann condensation Peer-reviewed

    Naoki Mori, Chiaki Mase, Hidenori Watanabe, Hirosato Takikawa

    Tetrahedron Letters　59　(26)　2600-2603　2018/06/27

    Publisher: Elsevier Ltd

    DOI： 10.1016/j.tetlet.2018.05.069 　

    ISSN： 1873-3581 0040-4039

    eISSN： 1873-3581

  29. The membrane‐bound O ‐acyltransferase Ale1 transfers an acyl moiety to newly synthesized 2‐alkyl‐ sn ‐glycero‐3‐phosphocholine in yeast Peer-reviewed

    Shiho Morisada, Yusuke Ono, Teruhisa Kodaira, Hideyuki Kishino, Ryo Ninomiya, Naoki Mori, Hidenori Watanabe, Akinori Ohta, Hiroyuki Horiuchi, Ryouichi Fukuda

    FEBS Letters　592　(11)　1829-1836　2018/06

    Publisher: Wiley

    DOI： 10.1002/1873-3468.13103 　

    ISSN： 0014-5793

    eISSN： 1873-3468

  30. Challenges for the Synthesis of Azadirachtin Peer-reviewed

    Naoki Mori

    Journal of Synthetic Organic Chemistry, Japan　76　(5)　506-509　2018/05/01

    Publisher: The Society of Synthetic Organic Chemistry, Japan

    DOI： 10.5059/yukigoseikyokaishi.76.506 　

    ISSN： 0037-9980

    eISSN： 1883-6526

  31. Synthetic studies on optically active furofuran and diarylbutane lignans* Invited Peer-reviewed

    Naoki Mori

    Bioscience, Biotechnology, and Biochemistry　82　(1)　1-8　2018/01/02

    Publisher: Informa UK Limited

    DOI： 10.1080/09168451.2017.1407235 　

    ISSN： 0916-8451

    eISSN： 1347-6947

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    Abstract Lignans are a large class of naturally occurring secondary metabolites which are widely spread within the plant kingdom. Their diverse structures and variety of biological activities have fascinated organic chemists. For synthesizing optically active lignans, we have developed the novel asymmetric dimerization of cinnamic acid derivatives, and applied it to the enantioselective syntheses of furofuran lignans (yangambin, sesamin, eudesmin, caruilignan A) and diarylbutane lignans (sauriols A and B). This review summarizes the methodology of our asymmetric dimerization of cinnamic acid derivatives, and efficient total syntheses of furofuran and diarylbutane lignans reported by our and other groups.

  32. Structural Insights into the CotB2-Catalyzed Cyclization of Geranylgeranyl Diphosphate to the Diterpene Cyclooctat-9-en-7-ol Peer-reviewed

    Takeo Tomita, Seung-Young Kim, Kazuya Teramoto, Ayuko Meguro, Taro Ozaki, Ayako Yoshida, Yudai Motoyoshi, Naoki Mori, Ken Ishigami, Hidenori Watanabe, Makoto Nishiyama, Tomohisa Kuzuyama

    ACS Chemical Biology　12　(6)　1621-1628　2017/06/16

    Publisher: American Chemical Society

    DOI： 10.1021/acschembio.7b00154 　

    ISSN： 1554-8937 1554-8929

    eISSN： 1554-8937

  33. Synthesis of (−)-okundoperoxide and determination of the absolute configuration of natural (+)-okundoperoxide Peer-reviewed

    Naoki Mori, Daichi Sakoda, Hidenori Watanabe

    Tetrahedron Letters　58　(40)　3884-3886　2017

    Publisher: Elsevier Ltd

    DOI： 10.1016/j.tetlet.2017.08.064 　

    ISSN： 1873-3581 0040-4039

  34. Synthesis of (-)-Chamobtusin A from (+)-Dehydroabietylamine Peer-reviewed

    Naoki Mori, Kazuma Kuzuya, Hidenori Watanabe

    Journal of Organic Chemistry　81　(23)　11866-11870　2016/12/02

    Publisher: American Chemical Society

    DOI： 10.1021/acs.joc.6b02328 　

    ISSN： 1520-6904 0022-3263

    eISSN： 1520-6904

  35. Synthesis of Azadirachtin, an Insect Antifeedant Peer-reviewed

    Naoki Mori, Daisuke Itoh, Hidenori Watanabe

    Journal of Synthetic Organic Chemistry, Japan　74　(9)　903-912　2016

    Publisher: The Society of Synthetic Organic Chemistry, Japan

    DOI： 10.5059/yukigoseikyokaishi.74.903 　

    ISSN： 0037-9980

    eISSN： 1883-6526

  36. Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans Peer-reviewed

    Naoki Mori, Akiko Furuta, Hidenori Watanabe

    Tetrahedron　72　(51)　8393-8399　2016

    Publisher: Elsevier Ltd

    DOI： 10.1016/j.tet.2016.10.058 　

    ISSN： 1464-5416 0040-4020

  37. Asymmetric formal synthesis of azadirachtin Peer-reviewed

    Naoki Mori, Takeshi Kitahara, Kenji Mori, Hidenori Watanabe

    Angewandte Chemie - International Edition　54　(49)　14920-14923　2015

    Publisher: Wiley-VCH Verlag

    DOI： 10.1002/anie.201507935 　

    ISSN： 1521-3773 1433-7851

  38. An unsaturated aliphatic alcohol as a natural ligand for a mouse odorant receptor Peer-reviewed

    Keiichi Yoshikawa, Hiroaki Nakagawa, Naoki Mori, Hidenori Watanabe, Kazushige Touhara

    Nature Chemical Biology　9　(3)　160-162　2013/03

    Publisher: Springer Science and Business Media LLC

    DOI： 10.1038/nchembio.1164 　

    ISSN： 1552-4450 1552-4469

    eISSN： 1552-4469

  39. Synthesis of (±)-chamobtusin A by a presumed biomimetic aza-cyclization Peer-reviewed

    Kazuma Kuzuya, Naoki Mori, Hidenori Watanabe

    Organic Letters　12　(21)　4709-4711　2010/11/05

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/ol101846z 　

    ISSN： 1523-7060 1523-7052

    eISSN： 1523-7052

  40. β-Lactamase-type thioesterase catalyzes product release in atrochrysone synthesis by iterative type I Polyketide Synthase.

    Awakawa Takayoshi, Yokota Kosuke, Funa Nobutaka, Doi Fuminao, Mori Naoki, Watanabe Hidenori, Ohnishi Yasuo, Horinouchi Sueharu

    Symposium on the Chemistry of Natural Products, symposium papers　(52)　67-72　2010/09/01

    Publisher: Symposium on the chemistry of natural products

    DOI： 10.24496/tennenyuki.52.0_67 　

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    Fungal polyketide, known with structural deversity and various biological properties, are synthesized by iteractive type I polyketide synthase (PKS). We focused on the PKS which synthesizes emotion, ATEG_08451 in a filamentous fungi, Aspergillus terreus, here named "atrochrysone carboxylic acid synthase (ACAS)", is a non-reducing iterative type I PKS (NR-PKS) that does not contain Claisen cyclase/thioesterase domain (CLC/TE) domain. Because a CLC/TE domain is responsible for product release from NR-PKS, ACAS was predicted to have novel mechanism for product release. In vitro, reactions of ACAS wigh malonyl-CoA yielded a polyketide intermediate, probably attached to its acyl carrier protein (ACP). The addition of ATEG_08450, here named "Atrochrysone carboxyl ACP thioesterase" (ACTE), to the reaction resulted in the release of products derived from atrochrysone carboxylic acid, such as atrochrysone, endocrocin anthrone, endocrocin, emodin anthrone and emodin. Atrochrysone carboxyliic acid decarboxylates to yield atrochrysone, and dehydrates to yield indocrocin anthrone. Atrochrysone dehydrates to yield emodin anthrone. Endocrocin anthrone and emodin anthrone auto-oxidize to form endocrocin and emodin. ACTE, belonging to the β-Lactamase superfamily, thus appears to be a novel type of thioesterase responsible for product release in polyketide biosynthesis. These findings show that ACAS synthesizes the scaffold of atrochrysone carboxylic acid from malonyl-CoA and that ACTE hydrolyzes the thioester bond between the ACP of ACAS and the intermediate to release atrochrysone carboxylic acid as the reaction product.

  41. Physically Discrete β-Lactamase-Type Thioesterase Catalyzes Product Release in Atrochrysone Synthesis by Iterative Type I Polyketide Synthase Peer-reviewed

    Takayoshi Awakawa, Kosuke Yokota, Nobutaka Funa, Fuminao Doi, Naoki Mori, Hidenori Watanabe, Sueharu Horinouchi

    Chemistry and Biology　16　(6)　613-623　2009/06/26

    Publisher: Elsevier BV

    DOI： 10.1016/j.chembiol.2009.04.004 　

    ISSN： 1074-5521

  42. Synthetic study towards azadirachtin: An efficient and stereoselective construction of the AB rings with full functionality Peer-reviewed

    Hidenori Watanabe, Naoki Mori, Daisuke Itoh, Takeshi Kitahara, Kenji Mori

    Angewandte Chemie - International Edition　46　(9)　1512-1516　2007

    Publisher: Wiley

    DOI： 10.1002/anie.200604097 　

    ISSN： 1433-7851

    eISSN： 1521-3773

  43. Simple synthesis of enantiomerically pure sauriols A and B Peer-reviewed

    Naoki Mori, Hidenori Watanabe, Takeshi Kitahara

    Bioscience, Biotechnology and Biochemistry　70　(7)　1750-1753　2006

    Publisher: Informa UK Limited

    DOI： 10.1271/bbb.60094 　

    ISSN： 0916-8451 1347-6947

    eISSN： 1347-6947

  44. Simple and Efficient Asymmetric Synthesis of Furofuran Lignans Yangambin and Caruilignan A Peer-reviewed

    Hidenori Watanabe, Naoki Mori, Takeshi Kitahara

    Synthesis　(3)　400-404　2006

    Publisher: Georg Thieme Verlag KG

    DOI： 10.1055/s-2006-926271 　

    ISSN： 0039-7881

    eISSN： 1437-210X

  45. 11 Synthetic Study on Azadirachtin, a Potent Insect Antifeedant

    Mori Naoki, Itoh Daisuke, Kitahara Takeshi, Mori Kenji, Watanabe Hidenori

    Symposium on the Chemistry of Natural Products, symposium papers　(47)　61-66　2005/09/15

    Publisher: Symposium on the chemistry of natural products

    DOI： 10.24496/tennenyuki.47.0_61 　

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    Azadirachtin (1) is a C-seco-limonoid isolated from the neem tree Azadirachta indica A. Juss (Meliaceae) and possesses potent antifeedant and growth inhibitory activities. Its complicated structure as well as its activities fascinate synthetic chemists and many synthetic efforts have been made, but the total synthesis of Azadirachtin has not been reported yet. Now we achieved a synthesis of model compound 2 which was fully functionalized at the dacalin moiety using an intramolecular Diels-Alder reaction and a radical cyclization as key reactions. In order to construct A-ring and the bridged ether, the intramolecular Diels-Alder reactions of 12 and 15 were examined, but the desired endo adducts 13 and 16 were obtained in low selectivity. So we devised the Diels-Alder reaction-decarboxylation-Claisen rearrangement strategy to use the undesired exo adduct. The intramolecular Diels-Alder reaction of 37 gave a cyclization-decarboxylation product 38 which was converted into 39 through Claisen rearrangement. In this process one carbon atom which was lost by decarboxylation could be recovered. The correct stereochemistries at C-3 and C-4 positions of Azadirachtin was introduced by oxidative cleavage of hydroxycyclohexenone ring followed by ozonolysis and aldol reaction (40→43). B-ring formation was then examined and radical cyclization (48→2) was found to proceed smoothly with controlling the newly-introduced stereochemistries. In summary, model compound 2, which had a fully functionalized decalin unit of Azadirachtin, was synthesized efficiently in short steps (19 steps). Other possible modes of radical cyclization such as 50→52 and 51→52 toward the total synthesis of Azadirachtin are now under investigations.

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Research Projects 4

  1. Development of a new synthetic method for multisubstituted tetrahydrofuran rings based on skeletal transformation of natural molecules

    Mori 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: Tohoku University

    2019/04/01 - 2022/03/31

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    Using sesamin, a naturally available furofuran lignan, as a synthetic element, we aimed to develop stereoselective synthesis of multisubstituted tetrahydrofuran rings and to synthesize zanthiplanispine by finding a new chemical transformation focusing on the reactivity at the benzylic position. Although the Baeyer-Villiger-type rearrangement with controlling selectivity of the rearrangement group at the benzylic position and the dehydrogenation reaction at the benzylic position proved difficult to achieve, the lactone obtained by MeReO3 oxidation was suggested to be an important intermediate that could lead to the synthesis of other lignans.

  2. Studies toward the total synthesis of pseudolaric acid B

    MORI 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: The University of Tokyo

    2016/04/01 - 2019/03/31

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    I have studied for the total synthesis of pseudolaric acid B, which would be a lead compound for developing novel anticancer agents. The most difficult issue in the synthesis of pseudolaric acid B is the construction of the trans-fused [5-7] ring system. I have used Dieckmann condensation as the key reaction to efficiently construct this unique structure.

  3. Development of the rational method for the synthesis of bioactive cyclic peroxides

    MORI NAOKI

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Young Scientists (B)

    Institution: The University of Tokyo

    2012/04/01 - 2014/03/31

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    Bioactive cyclic peroxides are expected to be candidates for new drugs such as antimalarial and anticancer agents. I aimed to develop the rational method for the synthesis of these peroxides and studied the synthrsis of okundoperoxide. I developed the stereoselective introduction method of peroxide unit by employing the Diels-Alder reaction between silyl dienyl ether and singlet oxygen. First asymmetric total synthesis of okundoperoxide has also been accomplished by using this method.

  4. Studies for the efficient synthesis of bioactive terpenoids

    MORI Naoki

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Young Scientists (B)

    Institution: The University of Tokyo

    2009 - 2010

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    I have studied for the efficient synthesis of bioactive terpenoids (azadirachtin and chamobtusin A). Construction of the full carbon skeleton of azadirachtin has been accomplished by using tandem radical cyclization in very short steps. Total synthesis of chamobtusin A has also been accomplished by using intramolecular aza-Michael cyclization as a key reaction.