Synthesis of (+)-coronafacic acid

J Org Chem. 2009 Mar 20;74(6):2433-7. doi: 10.1021/jo802493k.

Abstract

An enantioselective synthesis of (+)-coronafacic acid has been achieved. Rhodium-catalyzed cyclization of an alpha-diazoester provided the intermediate cyclopentanone in high enantiomeric purity. Subsequent Fe-mediated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was hydrogenated and carried on to the natural product.

Publication types

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

MeSH terms

  • Biological Products / chemical synthesis
  • Catalysis
  • Cyclization
  • Cyclopentanes
  • Hydrogenation
  • Indenes / chemical synthesis*
  • Rhodium
  • Stereoisomerism

Substances

  • Biological Products
  • Cyclopentanes
  • Indenes
  • cyclopentanone
  • coronafacic acid
  • Rhodium