Stereoselective oxidative coupling of methyl trans-ferulate by Trametes versicolor

Chemoenzymatic strategies for synthesizing complex molecules have been raised by combining biocatalytic and synthetic methods in a multistep approach toward a target molecule. Dihydrobenzofuran neolignans (DBNs) are a class of plant-derived natural compounds that display several biological activities. They are commonly obtained in low yields and without stereochemistry control through the oxidative coupling of phenylpropanoids. This study reports the novel eco-friendly, and regio- and diastereoselective conversion of methyl trans-ferulate (1) into DBN 2 ((±)-trans-dehydrodiferulate dimethyl ester) promoted by Trametes versicolor FC. The biotransformation approach afforded DBN 2 in 47% yield, with an interesting enantioselectivity compared to Ag2O-promoted oxidative coupling, as confirmed by chiral-HPLC analyses.