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生理活性ジテルペン類の高効率的キラル合成

Research Project

Project/Area Number 05234202
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Research InstitutionHokkaido University

Principal Investigator

白濱 晴久  北海道大学, 理学部, 教授 (00000802)

Co-Investigator(Kenkyū-buntansha) 松田 冬彦  北海道大学, 理学部, 講師 (10219446)
Project Period (FY) 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 1993: ¥2,400,000 (Direct Cost: ¥2,400,000)
Keywordsジテルペン / グラヤノトキシン / ビニグロール / ヨウ化サマリウム(II) / ケチルラジカル環化反応
Research Abstract

グラヤノトキシンIII(1)の全合成を達成した.先に合成したCD環部分(2)からアリルスルフィド(3)に導き,SmI_2によるケチルラジカル環化反応によりA環部分を立体選択的に作った.さらに,ケトアルデヒド(4)とし,SmI_2を用いて立体選択的ピナコール環化反応を行い,B環部分を構築,1の全合成に成功した.また,ビニグロール(5)の合成研究を行い,シス-デカリン骨格の構築方法を確立した.ジヒドロカルボン(6)よりケトエステル(7)を合成し,SmI_2によるケチルラジカル環化反応を行い,目的のシス-デカリン(8)のみを得た.

Report

(1 results)
  • 1993 Annual Research Report

Research Products

(8 results)

All Other

All Publications (8 results)

  • [Publications] T.Kan,S.Hosokawa,F.Matsuda,H.Shirahama: "Total Synthesis of (-)-Grayanotoxin III" J.Am.Chem.Soc.(in press).

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Kan,S.Nara,F.Matsuda,H.Shirahama: "Stereoselective Cyclization Mediotul by SmI_2" J.Org.Chem.(in press).

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Kan,M.Oikawa,F.Matsuda,H.Shirahama: "Stereocontrolled Construction of CD-Ring of Grayanotoxins" J.Org.Chem.(in press).

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Kito,T.Sakai,F.Matsuda,H.Shirahama: "Stereoselective Formation of trans-Decaline and is Decaline Skeletons" Synlett. 158-160 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Kan,M.Yanagiya,F.Matsuda,H.Shirahama: "Stereocontrolled Construction of B-Ring of Grayanotoxins" Synlett. 391-390 (1991)

    • Related Report
      1993 Annual Research Report
  • [Publications] Y.Morimoto,F.Matsuda,H.Shirahama: "Total Synthesis of (±)-Virantomycin" Synlett. 201-203 (1991)

    • Related Report
      1993 Annual Research Report
  • [Publications] F.Matsuda,H.Shirahama: "A New Look at Natural Products Chemistry in Three-Dimension" VHC Publishers,Inc., 23 (1992)

    • Related Report
      1993 Annual Research Report
  • [Publications] 松田冬彦: "高度に官能基化された天然有機化合物の全合成" 有機合成化学協会, 10 (1993)

    • Related Report
      1993 Annual Research Report

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Published: 1993-03-31   Modified: 2016-04-21  

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