Total Synthesis of Virgatolide B via Exploitation of Intramolecular Hydrogen Bonding

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dc.contributor.author Hume, Paul en
dc.contributor.author Furkert, Daniel en
dc.contributor.author Brimble, Margaret en
dc.date.accessioned 2016-07-25T04:21:57Z en
dc.date.issued 2014-06-06 en
dc.identifier.citation The Journal of Organic Chemistry, 2014, 79 (11), pp. 5269 - 5281 (13) en
dc.identifier.issn 0022-3263 en
dc.identifier.uri http://hdl.handle.net/2292/29584 en
dc.description.abstract A full account of the enantioselective total synthesis of virgatolide B is reported. Key features of the synthesis include an sp3–sp2 Suzuki–Miyaura cross-coupling of a β-trifluoroboratoamide with an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction. Intramolecular hydrogen bonding governed the regioselectivity of the key spiroketalization step, affording the natural product as a single regioisomer. en
dc.description.uri http://www.ncbi.nlm.nih.gov/pubmed/24836848 en
dc.language English en
dc.publisher American Chemical Society en
dc.relation.ispartofseries The Journal of Organic Chemistry en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0022-3263/ http://pubs.acs.org/page/copyright/index.html en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title Total Synthesis of Virgatolide B via Exploitation of Intramolecular Hydrogen Bonding en
dc.type Journal Article en
dc.identifier.doi 10.1021/jo5008527 en
pubs.issue 11 en
pubs.begin-page 5269 en
pubs.volume 79 en
dc.description.version VoR - Version of Record en
dc.rights.holder en
dc.identifier.pmid 24836848 en
pubs.author-url http://pubs.acs.org/doi/abs/10.1021/jo5008527 en
pubs.end-page 5281 en
pubs.publication-status Published en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 439820 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
dc.identifier.eissn 1520-6904 en
pubs.record-created-at-source-date 2016-07-04 en
pubs.online-publication-date 2014-05-16 en
pubs.dimensions-id 24836848 en


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