Synthesis of (±)-aureol by bioinspired rearrangements

J Org Chem. 2015 Feb 6;80(3):1866-70. doi: 10.1021/jo502841u. Epub 2015 Jan 27.

Abstract

A bioinspired and sustainable procedure for the straightforward synthesis of (±)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarnesol derivative and a biosynthetically inspired sequence of 1,2-hydride and methyl shifts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biochemical Phenomena
  • Catalysis
  • Cyclization
  • Epoxy Compounds / chemistry*
  • Farnesol / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism

Substances

  • Epoxy Compounds
  • Organometallic Compounds
  • Sesquiterpenes
  • aureol
  • titanocene
  • Farnesol