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Total synthesis of spirolide C for elucidation of its potent inhibitory mechanism on acetylcholine receptors

Research Project

Project/Area Number 24710249
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Living organism molecular science
Research InstitutionOsaka University

Principal Investigator

TSUCHIKAWA HIROSHI  大阪大学, 理学(系)研究科(研究院), 助教 (30460992)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsスピロリド / スピロアセタール / Diels-Alder反応 / 構造解析 / 化学合成 / スピロイミン / 全合成 / 構造決定
Outline of Final Research Achievements

For total synthesis of spirolide C, the synthesis of two main structures (6,5,5-bisspiroacetal unit and 7,6-spiroimine unit) has been investigated. First, the synthesis of 6,5,5-bisspiroacetal was attempted via the conformationally-restricted spirocyclization using a linker-tethered precursor. Although the key spirocyclization resulted in the selective formation of the undesired isomer, the important knowledge such as how to analyze the structure of products was obtained, which should be informative for future development. Next, for the construction of the 7,6-spiroimine unit, the selective Diels-Alder reaction using 2-silyl-dienyne and alfa-methylene-epsilon-lactam was successfully developed to give the desired exo-cycloadduct with high selectivity.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (8 results)

All 2015 2014 2013 Other

All Presentation (8 results)

  • [Presentation] 配座制御による立体選択的アセタール化反応を鍵としたスピロリドCのスピロアセタール環部分の合成研究2015

    • Author(s)
      安川佳史・土川博史・脇坂智広・村田道雄
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      東京
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Stereoselective Construction of 6,5,5-Bis-spiroacetal Ring of Spirolide C2014

    • Author(s)
      Yoshifumi Yasukawa, Tomohiro Wakisaka, Hiroshi Tsuchikawa and Michio Murata
    • Organizer
      The 4th Junior International Conference on Cutting-Edge Organic Chemistry in Asia (JICCEOCA-4)
    • Place of Presentation
      Thailand
    • Year and Date
      2014-11-28 – 2014-12-01
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋生物毒スピロリドCの全合成を目指した6,5,5-ビススピロアセタール環の合成研究2014

    • Author(s)
      安川佳史、脇坂智広、土川博史、村田道雄
    • Organizer
      第34回有機合成若手セミナー
    • Place of Presentation
      大阪
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] 海洋生物毒スピロリドCのスピロイミン環部分の効率的合成を目指した選択的Diels-Alder反応の検討2014

    • Author(s)
      林 翔・土川博史・松森信明・村田道雄
    • Organizer
      第94春季年会
    • Place of Presentation
      愛知県 名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Stereocontrolled synthesis of the 5,5,6-bisspiroacetal ring moiety of spirolide C2013

    • Author(s)
      Hiroshi Tsuchikawa, Tomohiro Wakisaka, Yoshifumi Yasukawa, Michio Murata
    • Organizer
      The First Asian Conference for“MONODUKURI”Strategy by Synthetic Organic Chemistry
    • Place of Presentation
      Okinawa, JAPAN
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋生物毒スピロリドCのA,E,F環部分の効率的合成を目指した選択的Diels-Alder反応の検討2013

    • Author(s)
      林 翔・土川博史・松森信明・村田道雄
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      東京都 タワーホール船堀
    • Related Report
      2013 Research-status Report
  • [Presentation] 海洋生物毒スピロリドCの全合成に向けた5,5,6-ビススピロケタール環部分の構築2013

    • Author(s)
      脇坂智広、土川博史、松森信明、村田道雄
    • Organizer
      第93春季年会
    • Place of Presentation
      滋賀県、立命館大学
    • Related Report
      2012 Research-status Report
  • [Presentation] 海洋生物毒 Spirolide Cの全合成を目指した 5,5,6-ビススピロケタール環部分の構築

    • Author(s)
      脇坂智広、土川博史、梅川雄一、松森信明、村田道雄
    • Organizer
      第32回有機合成若手セミナー
    • Place of Presentation
      兵庫県 神戸薬科大学
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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