Total synthesis of (+)-angelmarin

J Org Chem. 2009 Jul 17;74(14):5083-6. doi: 10.1021/jo900613u.

Abstract

An efficient 8-step enantioselective total synthesis of (+)-angelmarin, starting from commercially available umbelliferone, has been achieved. Key reactions include olefin cross-metathesis and a Shi epoxidation-cyclization sequence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Cyclization
  • Plant Extracts / chemical synthesis*
  • Plant Extracts / chemistry
  • Stereoisomerism
  • Umbelliferones / chemistry*

Substances

  • Coumarins
  • Plant Extracts
  • Umbelliferones
  • angelmarin
  • 7-hydroxycoumarin