Enantioselective synthesis of bicyclo[2.2.2]octenones using a copper-mediated oxidative dearomatization/[4 + 2] dimerization cascade

J Am Chem Soc. 2008 Mar 5;130(9):2738-9. doi: 10.1021/ja711018z. Epub 2008 Feb 12.

Abstract

An enantioselective approach to bicyclo[2.2.2]octenone structures utilizing a copper-mediated asymmetric oxidative dearomatization/[4 + 2] dimerization cascade is described. The total synthesis and absolute stereochemistry reassignment of (+)-aquaticol has been achieved using the methodology.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Copper / chemistry*
  • Cyclization
  • Cyclooctanes / chemical synthesis*
  • Cyclooctanes / chemistry
  • Dimerization
  • Molecular Conformation
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds
  • Cyclooctanes
  • Organometallic Compounds
  • Copper