Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated Claisen rearrangement and total synthesis of (+)-bakuchiol

Molecules. 2012 Nov 8;17(11):13330-44. doi: 10.3390/molecules171113330.

Abstract

An asymmetric Claisen rearrangement using Oppolzer’s camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.

MeSH terms

  • Acetates / chemistry
  • Hydrolysis
  • Molecular Conformation
  • Oxidation-Reduction
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Stereoisomerism
  • Sulfonamides / chemistry

Substances

  • Acetates
  • Phenols
  • Sulfonamides
  • bakuchiol