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■ Biomimetic Syntheses of Neurotrophic Americanol A and Isoamericanol A by Horseradish Peroxidase (HRP) Catalyzed Oxidative Coupling

Hironobu Takahashi, Keiji Matsumoto, Masumi Ueda, Youko Miyake, and Yoshiyasu Fukuyama*

*Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-cho, Tokushima 770-8514, Japan

Abstract

Horseradish peroxidase (HRP) catalyzed oxidative coupling of caffeic acid has yielded novel dimeric compounds (8) and (9) having a 1,4-benzodioxane ring, which have been in turn converted to americanol A (1) and isoamericanol A (2) in a few steps respectively. Additionally, HRP has coupled with 3,4-dihydroxycinnamyl alcohol giving rise directly 1 and 2 in high yield.