Simple synthesis of mite pheromone beta-acaridial and its analogs in the secretion of Caloglyphus polyphyllae (Acari: Acaridae)

Biosci Biotechnol Biochem. 2003 Aug;67(8):1732-6. doi: 10.1271/bbb.67.1732.

Abstract

A simple synthesis of beta-acaridial [(E)-1], the active principle of the sex, alarm and aggregation pheromone among astigmatid mites, was achieved in 5 steps from 1,2,4-butanetriol 2 in a 19% overall yield. Its analog, beta-acariolal 8, was also prepared in a 63% yield by oxidation of the intermediate, beta-acaridiol [(E)-7], with pyridinium dichromate (PDC). This synthetic route also gave beta-(Z)-acaridiol [(Z)-7] by using a Z-selective base in the Wittig reaction. (Z)-7 was oxidized to give a new monoterpene, beta-(Z)-acaridial [(Z)-1], which was detected as a trace component in the secretion of Caloglyphus polyphyllae, together with 8.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acari / chemistry*
  • Acari / physiology
  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Amino Alcohols / chemistry
  • Animals
  • Chromatography, Gas
  • Oxidation-Reduction
  • Sex Attractants / chemical synthesis
  • Sex Attractants / metabolism
  • Stereoisomerism

Substances

  • Aldehydes
  • Amino Alcohols
  • Sex Attractants
  • beta-acaridial