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

Shigefumi Kuwahara, Shiharu Hamade, Walter Soares Leal, Jiro Ishikawa, Osamu Kodama

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug (Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data of the synthetic sample with those of the natural material confirmed the proposed structure. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)8111-8117
Number of pages7
JournalTetrahedron
Volume56
Issue number41
DOIs
Publication statusPublished - 2000 Oct 6

Keywords

  • Cyclisation
  • Michael reactions
  • Pheromone
  • Terpenes and terpenoids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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