Synthesis of dl-Matairesinol Dimethyl Ether, Dehydrodimethylconidendrin and Dehydrodimethylretrodendrin from Ferulic Acid

Abstract

Dehydrodiferulic acid (II), a dimeric lactone obtainable from ferulic acid (I) by oxidative coupling, was converted into two types of lignans. Hydrogenolysis of II coupled with three subsequent operations gave dl-matairesinol dimethyl ether (IIIb). Acid-catalyzed cyclization of II followed by seven steps afforded dehydrodimethylconidendrin (X) and dehydrodimethylretrodendrin (XI).