Synthesis of both enantiomers of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas

Shigefumi Kuwahara, J. Ishikawa, W. S. Leal, S. Hamade, O. Kodama

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Synthesis of both enantiomers of a novel sesquiterpene, isolated as the putative sex pheromone of a Brazilian predatory stink bug (Tynacantha matginata Dallas) and proposed to have an unprecedented tricyclic carbon framework, was accomplished through an intramolecular Diels-Alder cyclization of a single optically active triene intermediate and separation of a pair of structural isomers derived from the resulting cycloadducts.

Original languageEnglish
Pages (from-to)1930-1935
Number of pages6
JournalSynthesis
Issue number13
DOIs
Publication statusPublished - 2000 Jan 1

Keywords

  • Cyclopentadienes
  • Diels-Alder reactions
  • Pheromones
  • Terpenoids
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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