Synthesis of syn-4,6-dimethyldodecanal, the male sex pheromone and trail-following pheromone of two species of the termite Zootermopsis

Nat Prod Res. 2011 Mar;25(5):560-8. doi: 10.1080/14786419.2010.535152.

Abstract

Recently, we reported that syn-4,6-dimethyldodecanal is the male sex pheromone and the trail-following pheromone of the Termopsidae Zootermopsis nevadensis and Zootermopsis angusticollis. In this article, we describe the syntheses of the mixture of the four stereoisomers of 4,6-dimethyldodecanal using a synthetic pathway where the key step is a Wittig reaction between methyl 4-methyl-5-oxo-pentanoate and 1-methylheptyl-triphenylphosphonium iodide, and of (±)-syn-4,6-dimethyldodecanal starting from 3,5-dimethyl-2-cyclohexen-1-one. Direct GC-MS comparison of these synthetic samples with the natural pheromone allowed its unambiguous identification.

MeSH terms

  • Animals
  • Gas Chromatography-Mass Spectrometry
  • Iodine Compounds / chemistry
  • Isomerism
  • Isoptera / chemistry*
  • Male
  • Molecular Structure
  • Pheromones / chemical synthesis*
  • Valerates / chemistry

Substances

  • Iodine Compounds
  • Pheromones
  • Valerates