Highly Regio- and Stereoselective Heck Reaction of Allylic Esters with Arenediazonium Salts: Application to the Synthesis of Kavalactones

Abstract

A highly efficient palladium-catalyzed Heck reaction of allylic esters with arenediazonium salts is described. The reaction proceeds under mild conditions, with excellent to total regio- and stereochemical control and with retention of the traditional leaving group. Furthermore, the generality of the present methodology is illustrated by the short total synthesis of the natural kavalactones, yangonine, (+/-)-methysticin, and (+/-)-dihydromethysticin.