A concise asymmetric synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl Acetate and propionate, the sex pheromones of pine sawflies

J Org Chem. 2004 May 28;69(11):3964-7. doi: 10.1021/jo0497961.

Abstract

(2S,3S,7S)-3,7-Dimethylpentadecan-2-yl acetate (2) and its propionate analogue (3) are the main sex pheromones of all Neodiprion species and Diprion similes, respectively. Starting from (S)-malic acid and employing a highly chemo-, regio-, and stereoselective tandem ester reduction-epoxide formation-reductive epoxide-opening reaction protocol, an efficient total synthesis of (2S,3S,7S)-2 and -3 is reported herein.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemical synthesis*
  • Alkanes / chemical synthesis*
  • Animals
  • Hymenoptera / chemistry*
  • Molecular Structure
  • Propionates / chemical synthesis*
  • Sex Attractants / chemical synthesis*

Substances

  • (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate
  • (2S,3S,7S)-3,7-dimethylpentadecan-2-yl propionate
  • Acetates
  • Alkanes
  • Propionates
  • Sex Attractants