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

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. © 2010 Royal Society of Chemistry.