Enantioselective total synthesis of (-)-nardoaristolone B via a gold(I)-catalyzed oxidative cyclization

Org Lett. 2015 Feb 6;17(3):461-3. doi: 10.1021/ol503531n. Epub 2015 Jan 7.

Abstract

The first enantioselective total synthesis of (-)-nardoaristolone B is accomplished by the implementation of an enantio- and diastereoselective copper(I)-catalyzed conjugate addition/enolate trapping sequence and a gold(I)-catalyzed oxidative cyclization (intermolecular oxidant), employed for the first time in total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Biological Products / pharmacology
  • Catalysis
  • Copper
  • Cyclization
  • Gold
  • Molecular Structure
  • Oxidation-Reduction
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology
  • Stereoisomerism

Substances

  • Biological Products
  • Sesquiterpenes
  • nardoaristolone B
  • Gold
  • Copper