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Unified total synthesis and biological evaluation of natural and artificial ryanoids

Research Project

Project/Area Number 15K14928
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionThe University of Tokyo

Principal Investigator

Inoue Masayuki  東京大学, 大学院薬学系研究科(薬学部), 教授 (70322998)

Research Collaborator NAGATOMO Masanori  東京大学, 大学院薬学系研究科, 助教 (70634161)
Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords合成化学 / 全合成 / 生物活性分子の設計 / 生理活性 / イオンチャネル / リアノジン / リアノジンレセプター
Outline of Final Research Achievements

Dysfunction of ion channels leads to various diseases. Rational development of pharmaceuticals that modulate functions of ion channels is an urgent task in modern science. Ryanodine receptors are calcium ion release channels, and are selectively activated by ryanodine. Our study aimed at unified total synthesis and biological evaluation of ryanodine, natural and artificial ryanoids.
In this study, we developed a new strategy for assembly of the architecturally complex structure of ryanodine, and achieved unified total synthesis of ryanodine and five other natural ryanoids. Our practical syntheses enabled us to prepare the ryanoids for detailed investigation of their various biological functions. Moreover, the fluorescent labeled ryanodine was prepared for investigation of the molecular interaction between the synthetic molecules and ryanodine receptors.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (31 results)

All 2017 2016 2015 Other

All Journal Article (7 results) (of which Peer Reviewed: 6 results,  Open Access: 1 results,  Acknowledgement Compliant: 5 results) Presentation (23 results) (of which Int'l Joint Research: 15 results,  Invited: 23 results) Remarks (1 results)

  • [Journal Article] Evolution of Radical-Based Convergent Strategies for Total Syntheses of Densely Oxygenated Natural Products2017

    • Author(s)
      M. Inoue
    • Journal Title

      Acc. Chem. Res.

      Volume: 50 Issue: 3 Pages: 460-464

    • DOI

      10.1021/acs.accounts.6b00475

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical Conversion of Ryanodol to Ryanodine2016

    • Author(s)
      Kengo Masuda, Masanori Nagatomo, Masayuki Inoue
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 7 Pages: 874-879

    • DOI

      10.1248/cpb.c16-00214

    • NAID

      130005160047

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Expanding the Scope of Et3B/O2-Mediated Coupling Reactions of O,Te-Acetal2016

    • Author(s)
      D. Kamimura,, M. Nagatomo, D. Urabe, M. Inoue
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 48 Pages: 7839-7848

    • DOI

      10.1016/j.tet.2016.04.023

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Symmetry-Driven Strategy for the Assembly of the Core Tetracycle of (+)-Ryanodine: Synthetic Utility of a Cobalt-Catalyzed Olefin Oxidation and α-Alkoxy Bridgehead Radical Reaction2016

    • Author(s)
      M. Nagatomo, K. Hagiwara, K. Masuda, M. Koshimizu, T. Kawamata, Y. Matsui, D. Urabe, M. Inoue
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 1 Pages: 222-229

    • DOI

      10.1002/chem.201503640

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Total Synthesis of (+)-Ryanodol and (+)-Ryanodine2016

    • Author(s)
      K. Masuda, M. Koshimizu, M. Nagatomo, M. Inoue
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 1 Pages: 230-236

    • DOI

      10.1002/chem.201503641

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Unified Total Synthesis of 3-epi-Ryanodol, Cinnzeylanol, Cinncassiols A and B, and Structural Revision of Natural Ryanodol and Cinnacasol2016

    • Author(s)
      M. Koshimizu, M. Nagatomo, M. Inoue
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 55 Issue: 7 Pages: 2493-2497

    • DOI

      10.1002/anie.201511116

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] リアノジン類の統一的全合成-多様性を志向した共通中間体の設計戦略2016

    • Author(s)
      長友優典, 井上将行
    • Journal Title

      化学

      Volume: 71 (4) Pages: 47-48

    • Related Report
      2015 Research-status Report
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2017

    • Author(s)
      M. Inoue
    • Organizer
      Cambridge-UTokyo Strategy Partnership Symposium on Chemistry and Chemical Biology
    • Place of Presentation
      東京大学(東京都, 文京区)
    • Year and Date
      2017-02-09
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 薬を創る化学2017

    • Author(s)
      井上将行
    • Organizer
      EMPプログラム, 東京大学
    • Place of Presentation
      東京大学(東京都, 文京区)
    • Year and Date
      2017-01-20
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] ラジカル反応の活用による複雑分子構築の単純化: 橋頭位ラジカルの利用2016

    • Author(s)
      井上将行
    • Organizer
      長崎大学大学院医歯薬学総合研究科
    • Place of Presentation
      長崎大学(長崎県, 長崎市)
    • Year and Date
      2016-11-11
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2016

    • Author(s)
      M. Inoue
    • Organizer
      The 1st PKU-WuXi AppTec Symposium of Organic Chemistry
    • Place of Presentation
      Peking University, Beijing, China
    • Year and Date
      2016-10-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 複雑な化合物を合成するときの合成戦略2016

    • Author(s)
      井上将行
    • Organizer
      化学技術基礎講座・製品開発に必要な有機合成化学の基礎
    • Place of Presentation
      日本化学会館(東京都, 千代田区)
    • Year and Date
      2016-10-07
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] ラジカル反応の活用による複雑分子構築の単純化2016

    • Author(s)
      井上将行
    • Organizer
      天然物談話会
    • Place of Presentation
      東映ホテル(新潟県, 南魚沼郡, 湯沢町)
    • Year and Date
      2016-07-08
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2016

    • Author(s)
      M. Inoue
    • Organizer
      ACP Lectureship
    • Place of Presentation
      Hong Kong University of Science and Technology, Hong Kong, China
    • Year and Date
      2016-05-25
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2016

    • Author(s)
      M. Inoue
    • Organizer
      ACP Lectureship
    • Place of Presentation
      The University of Hong Kong, Hong Kong, China
    • Year and Date
      2016-05-24
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2016

    • Author(s)
      M. Inoue
    • Organizer
      ACP Lectureship
    • Place of Presentation
      Chinese University of Hong Kong, Hong Kong, China
    • Year and Date
      2016-05-23
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ラジカル反応の活用による複雑分子構築の単純化2016

    • Author(s)
      井上将行
    • Organizer
      第5回 慶應義塾大学戦略的研究基盤形成支援事業シンポジウム, 有機合成化学ー効率化と環境調和性ー
    • Place of Presentation
      慶応義塾大学, 横浜
    • Year and Date
      2016-03-14
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      PACHIFICHEM
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-20
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ラジカル反応の活用による複雑分子構築の単純化: 橋頭位ラジカルの利用2015

    • Author(s)
      井上将行
    • Organizer
      東京農工大学大学院工学研究院
    • Place of Presentation
      東京農工大学, 東京
    • Year and Date
      2015-12-02
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      Cambridge-UTokyo Joint Symposium and Workshops
    • Place of Presentation
      Cambridge, UK
    • Year and Date
      2015-11-24
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      16th Tetrahedron Symposium Asia Edition
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2015-11-12
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      Tokyo-LMU Symposium
    • Place of Presentation
      LMU, Munich, Germany
    • Year and Date
      2015-10-29
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ラジカル反応の活用による複雑分子構築の単純化2015

    • Author(s)
      井上将行
    • Organizer
      公益財団法人乙卯研究所 創立100周年記念講演会
    • Place of Presentation
      ホテルKSP, 川崎
    • Year and Date
      2015-10-10
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      6th Japanese-Sino Symposium on Organic Chemistry for Young Chemists
    • Place of Presentation
      Akiu Resort Hotel Crescent, Sendai, Japan
    • Year and Date
      2015-09-08
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ラジカル反応の活用による複雑分子構築の単純化2015

    • Author(s)
      井上将行
    • Organizer
      有機合成夏期セミナー「明日の有機合成化学」
    • Place of Presentation
      大阪科学技術センター, 大阪
    • Year and Date
      2015-09-01
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      Kick-off Symposium on Advanced Research Network for Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Tohoku University, Sendai, Japan
    • Year and Date
      2015-08-25
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      45th World Chemistry Congress (IUPAC-2015)
    • Place of Presentation
      Busan, Korea
    • Year and Date
      2015-08-10
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      7th Pacific Symposium on Radical Chemistry
    • Place of Presentation
      Singapore
    • Year and Date
      2015-07-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      2nd EOC Symposium
    • Place of Presentation
      Nankai University, Tianjin, China
    • Year and Date
      2015-07-12
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical-Based Approach for Synthesis of Complex Natural Products2015

    • Author(s)
      M. Inoue
    • Organizer
      Burgenstock Conference
    • Place of Presentation
      Brunnen, Switzerland
    • Year and Date
      2015-05-01
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Remarks] 東京大学大学院薬学系研究科有機反応化学教室ホームページ

    • URL

      http://www.f.u-tokyo.ac.jp/~inoue/

    • Related Report
      2016 Annual Research Report 2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2018-03-22  

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