Strategies for the synthesis of fusicoccanes by Nazarov reactions of dolabelladienones: total synthesis of (+)-fusicoauritone

Angew Chem Int Ed Engl. 2007;46(6):915-8. doi: 10.1002/anie.200603853.

Abstract

A synthetic pathway leading to (+)-fusicoauritone (1) is highlighted by the use of a Julia condensation for preparation of an eleven-membered dolabelladienone precursor for subsequent Nazarov cyclization to yield the 5-8-5 tricyclic diterpene skeleton.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cyclization
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Conformation
  • Sensitivity and Specificity
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Diterpenes
  • Terpenes
  • dolabellane
  • fusicoauritone