Concise and enantioselective total synthesis of 15-deoxy-Δ-(12,14)-prostaglandin J(2)

J Org Chem. 2010 Nov 5;75(21):7458-60. doi: 10.1021/jo101523k.

Abstract

The concise and enantioselective synthesis of 15-deoxy-Δ(12,14)-prostaglandin J(2) (15d-PGJ(2)) has been accomplished in 11 steps from a known alcohol. The key step of the synthesis involves an asymmetric Rh-catalyzed cycloisomerization of ene-ynone, followed by an olefin isomerization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Prostaglandin D2 / analogs & derivatives*
  • Prostaglandin D2 / chemical synthesis
  • Prostaglandin D2 / chemistry
  • Rhodium / chemistry
  • Stereoisomerism
  • Substrate Specificity

Substances

  • 15-deoxy-delta(12,14)-prostaglandin J2
  • Rhodium
  • Prostaglandin D2