A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms

Chemistry. 2016 Aug 8;22(33):11597-600. doi: 10.1002/chem.201602669. Epub 2016 Jul 8.

Abstract

A short synthesis of the biologically active sesquiterpene natural product (+)-aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring-expanding Claisen rearrangement.

Keywords: Claisen rearrangement; aphanamol; conjugate addition; radical cyclization; total synthesis.

MeSH terms

  • Biological Products
  • Catalysis
  • Cyclization
  • Oxidation-Reduction
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry*
  • Stereoisomerism

Substances

  • Biological Products
  • Sesquiterpenes
  • aphanamol I