A concise, protection-free and divergent approach for the enantioselective syntheses of two pheromonal epoxide components of the fall webworm moth and other species

J Org Chem. 2010 Jul 2;75(13):4619-22. doi: 10.1021/jo1007042.

Abstract

On the basis of Zhou's modified Sharpless asymmetric epoxidation, sequential coupling reactions, and a divergent strategy, the protection-free syntheses of two main pheromonal components 1 and 5, found in the fall webworm moth, Hyphantria cunea, and other species have been accomplished in 10 steps (for two compounds). The overall yields are 31% for 1, 28% for 5, and 25% for both 1 and 5, respectively. The ee values of the final products 1 and 5 are at least 99%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Fatty Acids, Unsaturated / chemical synthesis*
  • Fatty Acids, Unsaturated / chemistry
  • Molecular Structure
  • Moths
  • Pheromones / chemical synthesis*
  • Pheromones / chemistry
  • Stereoisomerism

Substances

  • 9,10-epoxy-1,3,6-henicosatriene
  • 9,10-epoxy-3,6-henicosadiene
  • Epoxy Compounds
  • Fatty Acids, Unsaturated
  • Pheromones