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Studies on the synthesis of marine alkaloid spirolide D

Research Project

Project/Area Number 26860014
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionNagoya City University

Principal Investigator

YAMAKOSHI Hiroyuki  名古屋市立大学, 薬学研究科(研究院), 助教 (30596599)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsスピロリド類 / ジスピロケタール / アルカロイド / 渡環型反応 / テザー / 双極子モーメント / モレキュラーシーブ
Outline of Final Research Achievements

Toward the total synthesis of marine toxin spirolide D, the stereoselective construction of BCD fragment has been explored. Transannular spiroketalization of the triketone with a tether between the carboxyl group at C10 and hydroxyl group at C24 proceeded stereoselectively to give the desired stereoisomer in good yield. Since the reaction using acyclic triketone gave desired stereoisomer as the major product, the stereoselectivity of this process is rationalized by a preferred dipole orientation. The product was successfully converted to the BCD ring fragment through a stereoselective hydrogenation of C11-C12 double bond.

Report

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

    (7 results)

All 2015 2014

All Presentation (7 results) (of which Int'l Joint Research: 1 results)

  • [Presentation] Studies on the synthesis of spirolide D2015

    • Author(s)
      Akinori Toita, Keisuke Takeda, ○Hiroyuki Yamakoshi, Seiichi Nakamura
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM)
    • Place of Presentation
      米国ハワイ州ホノルル市
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 双極子制御に基づくスピロリドDの[6,5,5]ジスピロケタール環部の立体選択的合成2015

    • Author(s)
      戸井田明憲、竹田圭介、○山越博幸、橋本俊一、中村精一
    • Organizer
      日本病院薬剤師会東海ブロック日本薬学会東海支部合同学術大会2015
    • Place of Presentation
      愛知県名古屋市 金城学院大学
    • Year and Date
      2015-11-01
    • Related Report
      2015 Annual Research Report
  • [Presentation] 双極子モーメント制御に基づくスピロリド類ジスピロケタール環部の立体選択的合成2015

    • Author(s)
      戸井田明憲、竹田圭介、○山越博幸、橋本俊一、中村精一
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      大阪府東大阪市 近畿大学東大阪キャンパス
    • Year and Date
      2015-10-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] アセチルコリン受容体拮抗剤スピロリドDの合成研究(1)-渡環型ジスピロケタール化によるBCD環部の構築-2015

    • Author(s)
      戸井田明憲
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] スピロリドDの合成研究(2)-分子内ヘテロMichael反応によるBCD環構築-2015

    • Author(s)
      竹田圭介
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] アセチルコリン受容体拮抗剤スピロリドDの合成研究2014

    • Author(s)
      戸井田明憲
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      高知県立県民文化ホール
    • Year and Date
      2014-10-16
    • Related Report
      2014 Research-status Report
  • [Presentation] アセチルコリン受容体拮抗剤スピロリドDの合成研究-渡環反応によるBCD環構築-2014

    • Author(s)
      戸井田明憲
    • Organizer
      第60回日本薬学会東海支部総会・大会2014
    • Place of Presentation
      鈴鹿医療科学大学白子キャンパス
    • Year and Date
      2014-07-05
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2017-05-10  

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