Intramolecular Diels-Alder/Tsuji allylation assembly of the functionalized trans-decalin of salvinorin A

Org Lett. 2008 Jan 3;10(1):97-100. doi: 10.1021/ol7024058. Epub 2007 Dec 7.

Abstract

An enantioselective synthesis of the highly functionalized trans-decalin core (2) of salvinorin A is described. The tetraene 4 was synthesized in six steps from a known L-(+)-tartaric acid derivative. Three contiguous stereocenters, two of them quaternary, on the trans-decalin were established asymmetrically by an intramolecular Diels-Alder/Tsuji allylation sequence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes, Clerodane
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Stereoisomerism

Substances

  • Diterpenes
  • Diterpenes, Clerodane
  • Naphthalenes
  • decalin
  • salvinorin A