Concise syntheses of insect pheromones using Z-selective cross metathesis

Angew Chem Int Ed Engl. 2013 Jan 2;52(1):310-4. doi: 10.1002/anie.201206079. Epub 2012 Oct 10.

Abstract

Very short synthetic routes to nine cis-olefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported. These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Catalysis
  • Insecta
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Pheromones / chemical synthesis*
  • Pheromones / chemistry
  • Ruthenium / chemistry

Substances

  • Organometallic Compounds
  • Pheromones
  • Ruthenium