Laccase-catalyzed dimerization of hydroxystilbenes

Abstract

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 of the hydroxystilbenic moieties, followed by radical-radical coupling 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-α-β-5 (dihydrofuran-like) dimers. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.