ChemInform Abstract: A Novel Approach Towards Dibenzylbutyrolactone Lignans Involving Heck and Radical Reactions: Application to (.+‐.)‐Matairesinol Synthesis.

Abstract

±)-Matairesinol Synthesis. -A highly regioand stereoselective Heck reaction of iodoarenes to vinylated malonates is presented. The reaction provides a diversity of styrene and diarylbutene derivatives (V) in good yields. The transformation of these diarylbutenes into dibenzylbutyrolactones (VII)/ (VIII) and (X)/(XI) is achieved on two pathways involving radical cyclization of a selenylmethyl ester (VI) or a selenocarbonate (IX) as the key step. Lactone (VIIIa) is easily debenzylated to matairesinol (XII). -(SINGH, R.; SINGH, G. C.; GHOSH*, S. K.; Eur.