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A SYNTHETIC STUDY FOR OPTICALLY ACTIVE 2H-CHROMENE TRIMERS

Research Project

Project/Area Number 11640529
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTOYAMA UNIVERSITY

Principal Investigator

YAMAGUCHI Seiji  TOYAMA UNIVERSITY, FACULTY OF SCIENCE, ASSOCIATE PROFESSOR, 理学部, 助教授 (10018989)

Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2000: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1999: ¥700,000 (Direct Cost: ¥700,000)
KeywordsPYRANONAPHTHOQUINONES / 2H-CHROMENES / NAPHTHOQUINONES
Research Abstract

Natural conocurvone is an optically active pyranonaphthoquinone trimer, and the effective synthesis of conocurvone, consist of the effective preparation of a pyranotetralone as the key compond, the respective conversions of the pyranotetralone to the corresponding hydronaphthoquinone and naphthoquinone, and followed by trimerization of both monomeric naphthoquinones, two moles of the hydroxynaphthoquinone and one mole of the naphthoquinone. In the first year, the intramolecular cyclization of 2H-chromene-6-butanoic acids, prepared by acylation of some 2H-chromene with methyl hydrogensuccinate followed by reduction and hydrolysis, was found not to be effective for the preparation of the key pyranotetralone. In the second year, the thermal cyclization of the propargyl ether of 7-hydroxy-1-tetralone was found to be most effective for the key compound. Some tetralones having a naphtho[2, 1-b] pyran structure, were preprared by the regioselective thermal cyclization of the corresponding propargyl ethers. But, a similar preparation of the chiral pyranotetralone, having the prenyl side-chain was falied, because of racemization in the the propargyl etherification, and so the thermal cyclization gave the racemic pyranotetralone. The pyranotetralone, having a prenyl side-chain, and its dimethyl analog were converted respectively to the corresponding hydroxynaphthoquinones and naphthoquinones. Thus obtained hydroxyraphthoquinone and naphthoquinone, having the prenyl side-chain, thus prepared were identical with natural teretifolione B and its deoxy derivative. Trimerization of two mole of dimethylhydroxynaphthoquinone and one mole of dimethylnaphthoquinone gave the dimethyl analog of conocurvone. The ^1H NMR showed the existence of atrop isomerism.
The structural investigation for the dimethylanalogous trimer and the preparation of the chiral pyranotetralone are left to study.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (3 results)

All Other

All Publications (3 results)

  • [Publications] Seiji Yamaguchi: "Regioselective Cyclization of m-Acylaryl Propargyl Ethers Giving 5-Acyl-2, 2-dimethyl-2H-chromenes"Tetrahedron Letters. Vol.42,No.6. 1091-1093 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Yamaguchi: "Regioselective cyclization of m-acylaryl 1,1-dimethylpropargyl ethers giving 5-acyl-2, 2-dimethyl-2H-chromenes"Tetrahedron Lett.. Vol.42-No.6. 1091-1093 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Seiji Yamaguchi: "Regioselective Cyclization of m-Acylaryl Propargyl Ethers Giving 5-Acyl-2,2-dimethyl-2H-chromenes"Tetrahedron Letters. Vol.42,No.6. 1091-1093 (2001)

    • Related Report
      2000 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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