• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Preparation of An Optically Active Building Block Having A Quaternary Carbon Center and Synthesis of Euonyminol

Research Project

Project/Area Number 01540443
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionOkayama University of Science

Principal Investigator

UENISHI Junichi  Okayama Univ. of Sci. Faculty of Science, Lecture, 理学部, 講師 (50167285)

Co-Investigator(Kenkyū-buntansha) WAKABAYASHI Shoji  Okayama Univ. of Sci. Faculty of Science, Professor, 理学部, 教授 (40068870)
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1990: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1989: ¥1,100,000 (Direct Cost: ¥1,100,000)
Keywordsquaternary carbon / building block / PIFA / lipase / cyclization / euonyminol / acetomycin / ビルディングブロック / パ-ヨ-ドベンゼンジトリフルオロアセテ-ト / 環化学反応 / ミ-ノミノ-ル
Research Abstract

1. Preparation of optically active building blocks having a quaternary carbon center
(1) A various kinds of small building blockshaving a quaternary carbon center were synthesized from diethyl malonate by several steps.
(2) The utility of these building blocks was demonstrated by accomplishment of the total synthesis of anticancer antibiotics acetomycin.
(3) Although some attempts in preparation of optically active building blocks have benn failed, a kinetic resolution by lipase hydrolysis of some acetate derivatives having tetrahydrofuran ring, e. g. shown in the right, was successfully to give optical active alcohol. The highest degree of enantio excess become up to be 55-60 %.
2. Synthetic approaches to euonyminol
(1) A new aldol type of reaction between 1, 3-dithiane and ethyl vinyl ether mediated by PIFA (phenyliodosyl bistrifluoroacetate) was found, which was used for construction of the A ring of euonyminol.
(2) A key bond forming reaction in construction of the B ring was achieved by using SmI_2 mediated pinacol coupling reaction in the model substrates.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Junichi Uenishi, Yasuhiro Kawachi, Shoji Wakabayashi: "Synthesis of 6ーHydroxyー5,5ーdialkyl Substituted Cyclohenenones via (Bistrifluoroacetoxyiodo)benzene mediated Cyclization of 1,3ーDithiane and Ethyl Enol Ether" J. Chem. Soc., Chem. Commun.,. 1033-1034 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Junichi Uenishi, Takeshi Okadai, Shoji Wakabayashi: "Total Synthesis of (±)ーAcetomycin" Tetrahedron Letters. 32. 0000-0000 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Junichi Uenishi, Yasuhiro Kawachi and Shoji Wakabayashi: "Synthesis of 6-Hydroxy-5, 5-dialkyl Substituted Cyclohexenones via (Bistrifluoroacetoxyiodo) benzene mediated Cyclization of 1, 3-Dithiane and Ethyl Enol Ether" J. Chem. Soc., Chem. Commun.1033. (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Junichi Uenishi, Takeshi Okadai and Shoji Wakabayashi: "Total SYnthesis of (+)-Acetomycin" Tetrahedron Lett.32. 0000 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Junichi Uenishi;Yasuhiro Kawachi;Shoji Wakabayashi: "Synthesis of 6ーHydroxyー5,5ーdialkyl Substituted Cyclohexenones Via (Bistrifluoroacetoxyiodo)benzene mediated Cyclization of 1,3ーDithiane and Ethyl Enol Ether" J.Chem.Soc.,Chem.Commun.,. 1033-1034 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Junichi Uenishi;Takeshi Okadai;Shoji Wakabayashi: "Total Synthesis of (±)ーAcetomycin" Tetrahedron Letters. 32. (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] Junichi Uenishi,Yasuhiro kawachi,Shoji wakabayashi: "PIFA Mediated Intramolecular Aldol Reaction of Ethyl Enol Ether and 1,3-Dithiane:A New preparation of 5,5-Dialkylsubstituted Cyclohexenones" Tetrahedron Letters.

    • Related Report
      1989 Annual Research Report

URL: 

Published: 1989-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi