title: A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.
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.
authors: Department of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA).
authors: Bryan S
authors: BS
authors: Matsuura
authors: Mitchell H
authors: MH
authors: Keylor
authors: Bo
authors: B
authors: Li
authors: YuXuan
authors: Y
authors: Lin
authors: Shelby
authors: S
authors: Allison
authors: Derek A
authors: DA
authors: Pratt
authors: Corey R J
authors: CR
authors: Stephenson
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D032701:Biomimetics; D002460:Cell Line; D019281:Dimerization; D006801:Humans; D045563:Indolequinones / Q000737:chemistry; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000077185:Resveratrol; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000975:Antioxidants; D001688:Biological Products; D045563:Indolequinones; D011083:Polycyclic Compounds; D013267:Stilbenes; C535072:pallidol; C000603014:quadrangularin A; C068040:quinone methide; D000077185:Resveratrol
keywords: antioxidants; biomimetic synthesis; quinone methides; resveratrol; total synthesis
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