An intramolecular Diels-Alder approach to the eunicelins: enantioselective total synthesis of ophirin B

J Am Chem Soc. 2004 Aug 25;126(33):10264-6. doi: 10.1021/ja046574b.

Abstract

The enantioselective synthesis of the eunicellin ophirin B has been completed. A ring-closing metathesis provides efficient access to the oxonene ring, and a highly diastereoselective intramolecular Diels-Alder reaction results in the formation of the hydrobenzofuran portion of the molecule.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Stereoisomerism

Substances

  • Diterpenes
  • eunicellin
  • ophirin B