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Oxidation of hydroxy-alpha-methylcinnamate 5 derived from 4-methylesculetin afforded the alpha-methylcaffeoquinone derivative 7 without formation of the oxidative coupling product. The reaction of the alpha-methylferulate derivative 13 afforded a complex mixture of products. Thus, the hydroxy-alpha-methylcinnamates seem not to be suitable substrates for oxidative coupling. Compound 7 was tested for inhibitory effect on lipid peroxidation. It showed more potent activity than idebenone in rat brain homogenate, and was much more potent than (+/-)-alpha-tocopherol in rat liver microsomes.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Studies on the Preparation of Bioactive Lignans by Oxidative Coupling Reaction. VI. Oxidation of Methyl (E)-3-(4,5-Dihydroxy-2-methoxyphenyl)-2-butenoate and Lipid Peroxidation-Inhibitory Effects of the Produced Caffeoquinone.