Stereochemistry of phellinsin A: a concise synthesis of α-arylidene-γ-lactones

Abstract

Phellinsin A (1a) was prepared in a concise way, thereby elucidating the relative stereochemistry of the aryl and carboxylic acid groups in 1a. The synthesis employed selective monohydrolysis of the dilactones derived from oxidative dimerization of cinnamic acid derivatives. This approach provided a practical synthetic route to α-arylidene-γ-lactones.