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A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities
Authors:Bryan S. Matsuura  Mitchell H. Keylor  Bo Li  YuXuan Lin  Shelby Allison  Prof. Dr. Derek A. Pratt  Prof. Dr. Corey R. J. Stephenson
Affiliation:1. Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA);2. Department of Chemistry, University of Ottawa, Ottawa, ON K1N 6N5 (Canada)
Abstract:An efficient synthetic route to the resveratrol oligomers quadrangularin A and pallidol is reported. It features a scalable biomimetic oxidative dimerization that proceeds in excellent yield and with complete regioselectivity. A systematic evaluation of the natural products and their synthetic precursors as radical‐trapping antioxidants has revealed that, contrary to popular belief, this mode of action is unlikely to account for their observed biological activity.
Keywords:antioxidants  biomimetic synthesis  quinone methides  resveratrol  total synthesis
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