An efficient oxidative dearomatization-radical cyclization approach to symmetrically substituted bicyclic guttiferone natural products

Chem Commun (Camb). 2011 Jan 7;47(1):209-11. doi: 10.1039/c0cc01419b. Epub 2010 Jul 7.

Abstract

Detailed in this communication is an efficient synthetic approach towards the guttiferone family of natural products. Oxidatively unraveling a para-quinone monoketal followed by consecutive 5-exo radical cyclizations provides the bicyclic core. An additional strength of this approach is a late stage asymmetric desymmetrization of an advanced symmetric intermediate.

Publication types

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

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Computer Simulation
  • Cyclization
  • Free Radicals / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Phloroglucinol / analogs & derivatives*
  • Phloroglucinol / chemical synthesis
  • Phloroglucinol / chemistry
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Biological Products
  • Bridged Bicyclo Compounds
  • Free Radicals
  • Terpenes
  • guttiferone G
  • Phloroglucinol