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Synthesis and stereochemical assignment of (+)-chamuvarinin

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dc.contributor.authorFlorence, Gordon John
dc.contributor.authorMorris, Joanne Charleen
dc.contributor.authorMurray, Ross George
dc.contributor.authorOsler, Jonathan
dc.contributor.authorVanga, Raghava Reddy
dc.contributor.authorSmith, Terry K
dc.date.accessioned2011-03-10T16:26:08Z
dc.date.available2011-03-10T16:26:08Z
dc.date.issued2011-02-04
dc.identifier.citationFlorence , G J , Morris , J C , Murray , R G , Osler , J , Vanga , R R & Smith , T K 2011 , ' Synthesis and stereochemical assignment of (+)-chamuvarinin ' , Organic Letters , vol. 13 , no. 3 , pp. 514-517 . https://doi.org/10.1021/ol1028699en
dc.identifier.issn1523-7060
dc.identifier.otherPURE: 5052033
dc.identifier.otherPURE UUID: 8d348877-33dc-41b5-915c-5fa5833e5783
dc.identifier.otherWOS: 000286577600042
dc.identifier.otherScopus: 79851505529
dc.identifier.otherORCID: /0000-0001-9921-4399/work/56638879
dc.identifier.urihttps://hdl.handle.net/10023/1685
dc.descriptionSupported by grants from EPSRC (EP/F011458/1) and The Wellcome Trust (086658).en
dc.description.abstractA stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15−C28 ether array, followed by a late-stage Julia−Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin.
dc.format.extent4
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.rights(c)2011 American Chemical Society. This article is open access under the ACS AuthorChoice option.en
dc.subjectHydrolytic kinetic resolutionen
dc.subjectAnnonaceous acetogeninsen
dc.subjectUvaria-chamaeen
dc.subjectStereoisomer libraryen
dc.subjectRecent progressen
dc.subjectMosher methoden
dc.subjectBearingen
dc.subjectCondensationen
dc.subjectMechanismsen
dc.subjectMurisolinsen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleSynthesis and stereochemical assignment of (+)-chamuvarininen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Wellcome Trusten
dc.contributor.sponsorThe Royal Societyen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. School of Biologyen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1021/ol1028699
dc.description.statusPeer revieweden
dc.identifier.grantnumberEP/F011458/1en
dc.identifier.grantnumber086658 Z 08 Zen
dc.identifier.grantnumberUF090005en


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