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A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities
Author(s) -
Matsuura Bryan S.,
Keylor Mitchell H.,
Li Bo,
Lin YuXuan,
Allison Shelby,
Pratt Derek A.,
Stephenson Corey R. J.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409773
Subject(s) - resveratrol , regioselectivity , chemistry , antioxidant , combinatorial chemistry , yield (engineering) , organic chemistry , biochemistry , catalysis , materials science , metallurgy
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.