Laccase catalyzed dimerization of hydroxystilbenes

A series of hydroxystilbenes, analogues of the bioactive phytoalexin resveratrol, were synthesized and submitted to the catalytic action of a laccase from Trametes pubescens in a biphasic system made of ethyl acetate and acetate buffer. Oxidation took place at the 4’-hydroxy (4-hydroxy) position ofthe hydroxystilbenicm oieties, followed by radicalradicalcoupling dimerization reactions. Most of the products were isolated in good yields and fully characterized.Depending on the substrates, three different dimeric products could be identified, the main products usually being 4-O-a-ß-5 (dihydrofuran-like) dimers.