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dc.contributor.authorWu, Xiaoweien_US
dc.contributor.authorIwata, Takayukien_US
dc.contributor.authorScharf, Adamen_US
dc.contributor.authorQin, Tianen_US
dc.contributor.authorReichl, Kyle D.en_US
dc.contributor.authorPorco, John A.en_US
dc.date.accessioned2019-05-14T20:06:40Z
dc.date.available2019-05-14T20:06:40Z
dc.date.issued2018-05-09
dc.identifierhttp://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000432091700015&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=6e74115fe3da270499c3d65c9b17d654
dc.identifier.citationXiaowei Wu, Takayuki Iwata, Adam Scharf, Tian Qin, Kyle D Reichl, John A Porco. 2018. "Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling." JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Volume 140, Issue 18, pp. 5969 - 5975. https://doi.org/10.1021/jacs.8b02535
dc.identifier.issn0002-7863
dc.identifier.urihttps://hdl.handle.net/2144/35599
dc.description.abstractThe first synthesis of the chromanone lactone dimer gonytolide A has been achieved employing vanadium(V)-mediated oxidative coupling of the monomer gonytolide C. An o-bromine blocking group strategy was employed to favor para- para coupling and to enable kinetic resolution of (±)-gonytolide C. Asymmetric conjugate reduction enabled practical kinetic resolution of a chiral, racemic precursor and the asymmetric synthesis of (+)-gonytolide A and its atropisomer.
dc.description.sponsorshipWe thank the National Institutes of Health (R35 GM-118173) for research support. Work at the BU-CMD is supported by NIH R24 Grant GM-111625. We thank Prof. Scott Miller and Dr. Anthony Metrano (Yale University) for helpful discussions and preliminary experiments. We thank the Uehara Memorial Foundation for a postdoctoral fellowship to T.I., the American Cancer Society for a postdoctoral fellowship to K.D.R. (PF-16-235-01-CDD), Dr. Jeffrey Bacon (Boston University) for X-ray crystal structure analyses, and Prof. Haruhisa Kikuchi (Tohoku University) for providing a natural sample of gonytolide A. NMR (CHE-0619339) and MS (CHE-0443618) facilities at Boston University are supported by the NSF. (R35 GM-118173 - National Institutes of Health; GM-111625 - NIH; Uehara Memorial Foundation; PF-16-235-01-CDD - American Cancer Society; CHE-0619339 - NSF; CHE-0443618 - NSF)en_US
dc.format.extent5969 - 5975 (7)en_US
dc.languageEnglishen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofJOURNAL OF THE AMERICAN CHEMICAL SOCIETYen_US
dc.subjectScience & technologyen_US
dc.subjectPhysical sciencesen_US
dc.subjectChemistryen_US
dc.subjectChromonesen_US
dc.subjectHydrocarbons, brominateden_US
dc.subjectLactonesen_US
dc.subjectMolecular conformationen_US
dc.subjectOxidation-reductionen_US
dc.subjectVanadiumen_US
dc.subjectChemical sciencesen_US
dc.titleAsymmetric synthesis of gonytolide A: strategic use of an aryl halide blocking group for oxidative couplingen_US
dc.typeArticle
dc.identifier.doi10.1021/jacs.8b02535
pubs.elements-sourceweb-of-scienceen_US
pubs.notesEmbargo: Not knownen_US
pubs.organisational-groupBoston Universityen_US
pubs.organisational-groupBoston University, College of Arts & Sciencesen_US
pubs.organisational-groupBoston University, College of Arts & Sciences, Department of Chemistryen_US
pubs.publication-statusPublisheden_US
dc.identifier.mycv382335


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