Synthesis of the Bis-spiroacetal Moiety of Spirolides B and D

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dc.contributor.author Brimble, MA en
dc.contributor.author Meilert, Kai en
dc.date.accessioned 2011-09-21T22:32:12Z en
dc.date.issued 2005 en
dc.identifier.citation Org Lett 7(16):3497-3500 04 Aug 2005 en
dc.identifier.issn 1523-7060 en
dc.identifier.uri http://hdl.handle.net/2292/8216 en
dc.description.abstract An enantioselective synthesis of the bis-spiroacetal fragment of spirolides B and D is reported. The carbon framework was constructed via Barbier reaction of dihydropyran 3 with aldehyde 4, followed by a double oxidative radical cyclization to construct the bis-spiroacetal. A silyl-modified Prins cyclization and enantioselective crotylation successfully installed the stereocenters in the cyclization precursor. The initial unsaturated bis-spiroacetals 2a−d underwent equilibration during epoxidation to trans-epoxide 14 that was converted to a tertiary alcohol. en
dc.language EN en
dc.relation.ispartofseries Organic Letters 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/1523-7060/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject BIVALVE PINNA-MURICATA en
dc.subject SAKURAI ISMS REACTION en
dc.subject RELATIVE STEREOCHEMISTRY en
dc.subject SHELLFISH POISON en
dc.subject GYMNODIMINE en
dc.subject OXIDATION en
dc.subject ALCOHOLS en
dc.subject TOXINS en
dc.subject IDENTIFICATION en
dc.subject DINOFLAGELLATE en
dc.title Synthesis of the Bis-spiroacetal Moiety of Spirolides B and D en
dc.type Journal Article en
dc.identifier.doi 10.1021/ol051260u en
pubs.issue 16 en
pubs.begin-page 3497 en
pubs.volume 7 en
dc.rights.holder Copyright: 2005 American Chemical Society en
dc.identifier.pmid 16048326 en
pubs.end-page 3500 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 39896 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
pubs.record-created-at-source-date 2010-09-01 en
pubs.dimensions-id 16048326 en


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