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A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities
dc.contributor.authorMatsuura, Bryan S.en_US
dc.contributor.authorKeylor, Mitchell H.en_US
dc.contributor.authorLi, Boen_US
dc.contributor.authorLin, YuXuanen_US
dc.contributor.authorAllison, Shelbyen_US
dc.contributor.authorPratt, Derek A.en_US
dc.contributor.authorStephenson, Corey R. J.en_US
dc.date.accessioned2015-04-02T15:12:49Z
dc.date.available2016-05-10T20:26:28Zen
dc.date.issued2015-03-16en_US
dc.identifier.citationMatsuura, Bryan S.; Keylor, Mitchell H.; Li, Bo; Lin, YuXuan; Allison, Shelby; Pratt, Derek A.; Stephenson, Corey R. J. (2015). "A Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activities." Angewandte Chemie International Edition 54(12): 3754-3757.en_US
dc.identifier.issn1433-7851en_US
dc.identifier.issn1521-3773en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/110895
dc.description.abstractAn 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.Persistence pays off: A concise synthesis of the resveratrol oligomers quadrangularin A and pallidol was achieved by leveraging the persistence of 2,6‐di‐tert‐butyl phenol derived radical and quinone methide intermediates. Evaluation of these compounds as radical‐trapping antioxidants is presented and the results demonstrate that this mode of action is unlikely to account for the observed biological activity.en_US
dc.publisherWILEY‐VCH Verlagen_US
dc.subject.otherresveratrolen_US
dc.subject.othertotal synthesisen_US
dc.subject.otherbiomimetic synthesisen_US
dc.subject.otherantioxidantsen_US
dc.subject.otherquinone methidesen_US
dc.titleA Scalable Biomimetic Synthesis of Resveratrol Dimers and Systematic Evaluation of their Antioxidant Activitiesen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbtoplevelScienceen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)en_US
dc.contributor.affiliationotherDepartment of Chemistry, University of Ottawa, Ottawa, ON K1N 6N5 (Canada)en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/110895/1/anie_201409773_sm_miscellaneous_information.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/110895/2/3754_ftp.pdf
dc.identifier.doi10.1002/anie.201409773en_US
dc.identifier.sourceAngewandte Chemie International Editionen_US
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dc.owningcollnameInterdisciplinary and Peer-Reviewed


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