Studies on the Preparation of Bioactive Lignans by Oxidative Coupling Reaction. V. Oxidative Coupling Reaction of Methyl (E)-3-(2-Hydroxyphenyl)propenoate Derivatives and Lipid Peroxidation Inhibitory Effects of the Produced Lignans

Abstract

The oxidative coupling reactions of 2-hydroxycinnamates were investigated as a continuation of our previous studies on 4-hydroxy derivatives. The reaction of 2-hydroxycinnamate 1 and 2-hydroxy-4-methoxycinnamate 3 with silver oxide afforded polymerized lignin-like products, while that of 2-hydroxy-bis(methoxymethoxy)cinnamates 5 and 6, after acetylation, gave the enol acetates, 8 and 14, of oxotetrahydrobenzoxanthene derivatives, respectively. These two products were also obtained by the oxidation of 5 and 6 with potassium hexacyanoferrate(III). In the reactions of 5 and 6 with iron(III) chloride, the major products were the partially demethoxymethoxylated compounds 9 and 15, respectively. Thus, the course of the reactions in the oxidation of 2-hydroxycinnamates is quite different from that in the case of 4-hydroxy derivatives. The product 8 and the corresponding oxotetrahydrobenzoxanthene derivative were found to show moderate inhibitory effects upon lipid peroxidation. © 1995, The Pharmaceutical Society of Japan. All rights reserved.