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dc.contributor.authorPaterson, Ianen
dc.contributor.authorNg, Kenneth K-Hen
dc.contributor.authorWilliams, Simonen
dc.contributor.authorMillican, David Cen
dc.contributor.authorDalby, Stephen Men
dc.date.accessioned2014-10-17T14:49:58Z
dc.date.available2014-10-17T14:49:58Z
dc.date.issued2014-01-30en
dc.identifier.citationAngewandte Chemie International Edition, 53: 2692–2695. DOI: 10.1002/anie.201310164en
dc.identifier.issn1433-7851
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/246209
dc.description.abstractLeiodermatolide is an antimitotic macrolide isolated from the marine sponge Leiodermatium sp. whose potentially novel tubulin-targeting mechanism of action makes it an exciting lead for anticancer drug discovery. In pursuit of a sustainable supply, we report a highly stereocontrolled total synthesis (3.2 % yield) based on a convergent sequence of palladium-mediated fragment assembly and macrolactonization. Boron-mediated aldol reactions were used to configure the three key fragments 2, 5, and 6 by employing the appropriate enantiomer of the lactate-derived ketone 7.
dc.description.sponsorshipThis research was supported by a SCAST postgraduate research scholarship (K.K.-H.N.), the Todd-Raphael Fund (S.W.), and Clare College, Cambridge (S.M.D.). We thank Dr. Amy Wright (HBOI, Florida Atlantic University) for helpful discussions and the EPSRC UK National Mass Spectrometry Facility at Swansea University.
dc.languageEnglishen
dc.language.isoenen
dc.publisherWiley
dc.rightsAttribution 2.0 UK: England & Wales*
dc.rights.urihttp://creativecommons.org/licenses/by/2.0/uk/*
dc.subjectaldol reactionen
dc.subjectantitumor agentsen
dc.subjectcross-couplingen
dc.subjectmacrolidesen
dc.subjecttotal synthesisen
dc.titleTotal Synthesis of the Antimitotic Marine Macrolide (−)-Leiodermatolideen
dc.typeArticle
dc.description.versionThis is the final published version. It's also available from Wiley at http://onlinelibrary.wiley.com/doi/10.1002/anie.201310164/abstract.en
prism.endingPage2695
prism.publicationDate2014en
prism.publicationNameAngewandte Chemie International Editionen
prism.startingPage2692
prism.volume53en
dc.rioxxterms.funderEPSRC
rioxxterms.versionofrecord10.1002/anie.201310164en
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/all-rights-reserveden
rioxxterms.licenseref.startdate2014-01-30en
dc.contributor.orcidPaterson, Ian [0000-0002-8861-9136]
dc.identifier.eissn1521-3773
rioxxterms.typeJournal Article/Reviewen


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Attribution 2.0 UK: England & Wales
Except where otherwise noted, this item's licence is described as Attribution 2.0 UK: England & Wales