A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities |
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| Authors: | Bryan S. Matsuura Mitchell H. Keylor Bo Li YuXuan Lin Shelby Allison Prof. Dr. Derek A. Pratt Prof. Dr. Corey R. J. Stephenson |
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| 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) |
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| 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. |
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| Keywords: | antioxidants biomimetic synthesis quinone methides resveratrol total synthesis |
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