A concise synthesis of pawhuskin A

J Nat Prod. 2008 Nov;71(11):1949-52. doi: 10.1021/np800351c. Epub 2008 Oct 15.

Abstract

Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.

Publication types

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

MeSH terms

  • Fabaceae / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Stilbenes
  • Terpenes
  • pawhuskin A