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

Synthetic Studies on Polyquinane Sesquiterpenes

Research Project

Project/Area Number 63570992
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionOsaka University

Principal Investigator

IMANISHI Takeshi  Osaka Univ., Fac. of Pharm. Sci., Professor, 薬学部, 教授 (40028866)

Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1989: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1988: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsNatural product synthesis / Bond cleavage of cyclopronae ring / Sesquiterpene / Polyquinane / Pentalenene / Quadrone / 抗腫瘍活性 / クァドロン類縁体 / シクロプロパン / 全合成 / 立体選択性 / 制癌作用
Research Abstract

Polyquinane framework plays an important role of structural unit of many kinds of naturally occurring organic compounds, some of which exhibit significantly biological activities. In this project, a couple of poluquinane sesquiterpenes were successfully synthesized by the use of a common intermediate 1 which was subjected to regioselective C-C bond cleavage of cyclopropane ring.
The Birch reduction of 1 exclusively afforded the bicyclo 3.3.0 octane 2 via C_2-C_8 bond fission of the cyclopropane ring, while treatment of 1 under nucleophilic substitution conditions gave the bicyclo 3.2.1 octane 3 as a main product via the C_1-C_2 ond cleavage. On the other hand, the carboxylic acid 4, easily obtained from 1, afforded the lactone 5 efficiently through the exclusive C_1-C_2 bond fission by an intramolecular carboxylic acid participation.
Through the several-step sequence starting from 2, total synthesis of a representative triqyinane sesquiterpene pentalenene (6) was accomplished.
Descarboxyquadrone (7) and an antitumor diquinane sesquiterpene quardrone (9) were also synthesized by the use of key intermediates 3 and 8,respectively.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (18 results)

All Other

All Publications (18 results)

  • [Publications] Takeshi Imanishi et al.: "7,7-Dimethyltricyclo[3.3.0.0^<2,8>]octan-3-ones as Synthetic Intermediates.I.Preparation and Cyclopropane Ring Opening of 7,7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.0^<2,8>]octan-3-one" Chem.Pharm.Bull.36. 1351-1357 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi et al.: "7,7-Dimethyltricyclo[3.3.0.0^<2,8>]octan-3-ones as Synthetic Intermediates.II.A Total Synthesis of(±)-Pentalenene,Angular Triquinane Sesquiterpene" Chem.Pharm.Bull.36. 1371-1378 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi et al.: "7,7-Dimethyltricyclo[3.3.0.0^<2,8>]octan-3-ones as Synthetic Intermediates.III.Total Synthesis of(±)-Descarboxyquadrone" Chem.Pharm.Bull.36. 2012-2016 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi et al.: "7,7-Dimethyltricyclo[3.3.0.0^<2,8>]octan-3-ones as Synthetic Intermediates.IV.A Further Examination of Cyclopropane Ring Opening in the Tricyclo 3.3.0.0^<2,8> octan-3-one System" Chem.Pharm.Bull.37. 3114-3116 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi et al.: "7,7-Dimethyltricyclo[3.3.0.0^<2,8>]octan-3-ones as Synthetic Intermediates.V.An Improved Synthesis of(±)-Pentalenene" Chem.Pharm.Bull.38. (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi, Masayuki Yamashita, Fusako Ninbari, Tetsuaki Tanaka, and Chuzo Iwata: "7,7-Dimethyltricyclo 3.3.0.0^<2,8> octan-3-ones as Synthetic Intermediates. I. Preparation and Cyclopropane Ring Opening of 7,7-Dimethyl-5-(2-propenyl)tricyclo-3.3.0.0^<2,8> octan-3-one" Chem. Pharm. Bull.36. 1351-1357 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi, Masayuki Yamashita, Fusako Ninbari, Tetsuaki Tanaka, and Chuzo Iwata: "----- II. A Total Synthesis of (<plus-minus>)-Pentalenene, an Angular Triquinane Sesquiterpe " Chem. Pharm. Bull., 36, 1371-1378, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi, Masayuki Yamashita, Munetaka Matsui, Tetsuaki Tanaka, and Chuzo Iwata: "----- III. Total Synthesis of (<plus-minus>)-Descarboxyquadro " Chem. Pharm. Bull., 36, 2012-2016, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi, Masayuki Yamashita, Munetaka Matsui, Tetsuaki Tanaka, and Chuzo Iwata: "----- IV. A Further Examination of Cyclopropane Ring Opening in the Tricyclo 3.3.0.0^<2,8> octan-3-one System" Chem. Pharm. Bull., 37, 3114-3116, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi, Masayuki Yamashita, Yoshimi Hirokawa, Tetsuaki Tanaka, and Chuzo Iwata: "----- V. An Improved Synthesis of (<plus-minus>)-Pentalene " Chem. Pharm. Bull., 38.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Imanishi et al.: "7,7ーDimethytricyc1o[3.3.0.0^<2,8>]octanー3ーones as Synthetic Intermediates.I.Preparation and Cyclopropane Ring Opening of 7,7ーDimethy1ー5ー (2ーpropenyl)tricyclo[3.3.0.0^<2,8>]octanー3ーone" Chem.Pharm.Bull.36. 1351-1357 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Takeshi Imanishi et al.: "7,7ーDimethy1tricyclo[3.3.0.0^<2,8>]octanー3ーones as Synthetic Intermediates.II.a Total Synthesis of(±)ーPentalenene,an Angular Triquinane Sesquiterpene" Chem.Pharm.Bull.36. 1371-1378 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Takeshi Imanishi et al.: "7,7ーDimethyltricyclo[3.3.0.0^<2,8>]octanー3ーones as Synthetic Intermediates.III.Total Synthesis of(±)ーDescarboxyquadrone" Chem.Pharm.Bull.36. 2012-2016 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Takeshi Imanishi et al.: "7,7ーDimethyltricyclo[3.3.0.0^<2,8>]octanー3ーones as Synthetic Intermediates.IV.A Further Examination of Cyclopropane Ring Opening in the Tricyclo 3.3.0.0^<2,8> octanー3ーone System" Chem.Pharm.Bull.37. 3114-3116 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Takeshi Imanishi et al.: "7,7ーDimethyltricyclo[3.3.0.0^<2,8>]octanー3ーones as Synthetic Intermediates.V.An improved Synthesis of(±)ーPentalenene" Chem.Pharm.Bull.38. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Takeshi Imanishi: Chem.Pharm.Bull.36. 1351-1357 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Takeshi Imanishi: Chem.Pharm.Bull.36. 1371-1378 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Takeshi Imanishi: Chem.Pharm.Bull.36. 2012-2016 (1988)

    • Related Report
      1988 Annual Research Report

URL: 

Published: 1988-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi