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1989 Fiscal Year Final Research Report Summary

Synthetic Studies of Gloeosporone, A Self-Inhibitor for Germination of Spores of Colletotrichum gloeosporioides

Research Project

Project/Area Number 63570997
Research Category

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

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

Principal Investigator

IRIE Hiroshi  Professor, Nagasaki Univ. Faculty of Pharmaceutical Scie., 薬学部, 教授 (00025686)

Co-Investigator(Kenkyū-buntansha) UENO Tamio  Associate Prof. Kyoto Univ., Department of Agriculture, 農学部, 助教授 (20026579)
TAKEDA Shigeko  Research Assistant, Nagasaki Univ. Faculty of Pharmaceutical Scie., 薬学部, 助手 (50039640)
Project Period (FY) 1988 – 1989
KeywordsSpores of Fungus / Self-inhibito / Gloeosporone / Carbamate formation / Resolution / 天然物全合成
Research Abstract

Some spores of plant pathogenic fungi possess the compounds, named as self-inhibitor, which interfere the germination of spores. In 1982, Mayor and his coworkers reported the isolation of a self-inhibitor, gloeosporone, from the fungus Colletotrichum gloeosporioide. We aimed at the synthesis of the compound to investigate the structure-activity relationship.
In the first year of the grant, we accomplished the synthesis of gloeosporone as a racemic modification along with its diastereoisomer. Based on the result, we focused on the synthesis of these compounds in optically active forms. Application of Lewis acid catalysed preparation of the carbamates on (dl)-1-tridecene-8-ol with (S)-1-(1-naphthyl)ethyl isocyanate (Pirkle's reagent) gave a mixture of the diastereoisomeric carbamates. After separation of each isomer in pure form, the optically active 1-decene-8-ols were regenerated by reduction with lithium aluminum hydride. By tracing the procedure for synthesis of racemic gloeosporone, the synthesis of (+)- and (-)-gloeosporone and their stereoisomers were completed. The biological test of these compounds synthesized, however, have the weak activity as a self-inhibitor. The effort to disclose the discrepancy between the reported data and our results is under investigation.

  • Research Products

    (4 results)

All Other

All Publications (4 results)

  • [Publications] Hiroshi Irie: "Lewis Acid Catalysed Proparation of some Carbamates and Sulphonylureas. Application to the Determination of Enantiomeric purity of Chiral Alcohols" J.Chem.Soc.,Perkin Transaction I. 1989. 1209-1210 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tamio Ueno: "Studies in Natural Products Chemistry Vol.?(Edited by Atta-ur-Rahman)" Elsevier Amsterdam-Oxford-New York-Tokyo, (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroshi Irie, Masatska Nishimura, and Morihiro Yoshida: "Lewis Acid Catalysed Preparation of some Carbamates and Sulphonylureas. Application to the Determination of Enantiomeric Purity of Chiral Alcohols" J. Chem. Soc.Perkin Trans. I. 1209-1210 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tamio Ueno, Tetsu Tsurushima, Hiroshi Fukamin and Hiroshi Irie: Studies in Natural Products Chemistry Vol X Chemistry of Self-Inhibitors of Fungal Germination (Edited by Atta-ur-Rahman). Elsevier, Amsterdam-Oxford-New York- Tokyo, (1990)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-03-26  

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