Pheromone Synthesis, CLVII. Synthesis of the Enantiomers of syn‐4‐Methyl‐5‐nonanol to Determine the Absolute Configuration of the Naturally Occurring (4S,5S) Isomer Isolated as the Male‐produced Pheromone Compound of Rhynchophorus vulneratus and Metamasius hemipterus

Kenji Mori, Hiromasa Kiyota, Christian Malosse, Didier Rochat

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The enantioselective synthesis of both (4R,5R)‐ and (4S,5S)‐4‐methyl‐5‐nonanol (1) was achieved by starting from an optically active epoxide 5. A GC comparison on a chiral stationary phase of the synthetic enantiomers of 1 with the naturally occurring 1 was executed, and (4S,5S)‐1 was shown to be identical with the natural 1 isolated as the male‐produced pheromone compound of the weevils Rhynchophorus vulneratus and Metamasius hemipterus.

Original languageEnglish
Pages (from-to)1201-1204
Number of pages4
JournalLiebigs Annalen der Chemie
Volume1993
Issue number11
DOIs
Publication statusPublished - 1993
Externally publishedYes

Keywords

  • Asian palm weevil
  • Epoxides
  • Metamasiums hemipterus
  • Pheromones
  • Rhynchophorus vulneratus

ASJC Scopus subject areas

  • Medicine(all)

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