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Synthetic studies on aconitine toward creation of new analgesics

Research Project

Project/Area Number 25620088
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionWaseda University

Principal Investigator

Hosokawa Seijiro  早稲田大学, 理工学術院, 准教授 (10307712)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Keywordsアコニチン / 全合成研究 / 選択的合成 / モーヴァッサン還元 / アルドール反応 / 有機合成化学 / 全合成 / 立体選択的合成
Outline of Final Research Achievements

Synthetic studies on aconitine have been deployed. Aconitine was devided to AEF rings and BCDE rings and synthetic routes of both compounds have been researched. At first, E ring moiety has been synthesized as a common part of them. An aldehyde derived from E ring was found to give aldol adducts with a precursor of A ring by using Lewis acid-mediated aldol reaction. Additionally, in studies of cyclization to obtain A ring, it was found that an olefin-attached alpha-diazoketone gave a cyclized compound via a diazo-attached intramolecular [3+2] adduct. On the other hand, E ring was coupled with C ring in accompany with the stereoselective construction of a quaternary carbon. D ring was constructed by ring closure metathesis to give CDE ring skeleton.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (10 results)

All 2014 2013 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (6 results) (of which Invited: 3 results) Book (2 results) Remarks (1 results)

  • [Journal Article] Concise Synthesis of Reduced Propionates by Stereoselective Reduction Combined with the Kobayashi Reactions2013

    • Author(s)
      3. Tatsuya Nakamura, Mio Harachi, Takaaki Kano, Yuki Mukaeda, Seijiro Hosokawa
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 12 Pages: 3170-3173

    • DOI

      10.1021/ol401406m

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 全合成を短くする2014

    • Author(s)
      細川 誠二郎
    • Organizer
      平成26年度後期(秋季)有機合成化学講習会
    • Place of Presentation
      東京
    • Year and Date
      2014-11-20 – 2014-11-21
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] 抗生物質aculeximycinの全合成研究2014

    • Author(s)
      加藤 卓也・佐藤 友彦・細川 誠二郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] Aflastatin Aの全合成研究2013

    • Author(s)
      村越爽人・細川誠二郎
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] トリカブト毒アコニチンの合成研究2013

    • Author(s)
      中村竜也、細川誠二郎
    • Organizer
      第48回天然物談話会
    • Place of Presentation
      草津
    • Related Report
      2013 Research-status Report
  • [Presentation] Remote Asymmetric Induction Reactions for Natural Product Synthesis

    • Author(s)
      Seijiro Hosokawa
    • Organizer
      第2回千葉大学キラリティーネットワーク研究会講演会
    • Place of Presentation
      千葉
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Total Synthesis of Natural Products possessing the Substituted Quinone and Multiple Stereogenic Centers

    • Author(s)
      Seijiro Hosokawa
    • Organizer
      The 3rd Frontiers in Medicinal Chemistry
    • Place of Presentation
      ソウル
    • Related Report
      2013 Research-status Report
    • Invited
  • [Book] 有機合成実験法ハンドブック2014

    • Author(s)
      細川 誠二郎
    • Total Pages
      6
    • Publisher
      丸善株式会社
    • Related Report
      2013 Research-status Report
  • [Book] Synthesis of Drugs and Natural Products, Volume 12013

    • Author(s)
      Seijiro Hosokawa
    • Total Pages
      33
    • Publisher
      John Weily & Sons Inc.
    • Related Report
      2013 Research-status Report
  • [Remarks] 早稲田大学 細川研究室

    • URL

      http://www.waseda.jp/sem-hosokawalab/

    • Related Report
      2015 Annual Research Report

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Published: 2014-07-25   Modified: 2019-07-29  

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