A non-iterative, flexible, and highly stereoselective synthesis of polydeoxypropionates--synthesis of (+)-vittatalactone

Chem Commun (Camb). 2011 Mar 21;47(11):3248-50. doi: 10.1039/c0cc05215a. Epub 2011 Jan 28.

Abstract

A short sequence comprising an oxy-Cope rearrangement, iridium-catalyzed hydrogenation, and enolate methylation provides trideoxypropionates with excellent diastereocontrol. A straightforward synthesis of the cucumber beetle pheromone (+)-vittatalactone illustrates this new strategy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Catalysis
  • Coleoptera / chemistry
  • Hydrogenation
  • Iridium / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Pheromones / chemistry
  • Stereoisomerism

Substances

  • Lactones
  • Pheromones
  • vittatalactone
  • Iridium