A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)

Shigefumi Kuwahara, Daisuke Itoh, Walter Soares Leal, Osamu Kodama

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

(2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.

Original languageEnglish
Pages (from-to)11421-11430
Number of pages10
JournalTetrahedron
Volume54
Issue number38
DOIs
Publication statusPublished - 1998 Sep 17
Externally publishedYes

Keywords

  • Olefination
  • Pheromones
  • Sulfur compound
  • Terpenes and terpenoids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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