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.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Antioxidants / chemical synthesis
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Antioxidants / chemistry*
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Antioxidants / metabolism
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Biological Products / chemical synthesis
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Biological Products / chemistry
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Biomimetics
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Cell Line
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Dimerization
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Humans
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Indolequinones / chemistry
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Oxidation-Reduction
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Polycyclic Compounds / chemical synthesis*
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Polycyclic Compounds / chemistry
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Polycyclic Compounds / metabolism
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Resveratrol
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Stereoisomerism
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Stilbenes / chemical synthesis*
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Stilbenes / chemistry*
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Stilbenes / metabolism
Substances
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Antioxidants
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Biological Products
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Indolequinones
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Polycyclic Compounds
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Stilbenes
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pallidol
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quadrangularin A
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quinone methide
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Resveratrol