Enantioselective Synthesis of the Dimeric Pyranonaphthoquinone Core of the Cardinalins Using a Late-Stage Homocoupling Strategy

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dc.contributor.author Sperry, Jonathan en
dc.contributor.author Gibson, JS en
dc.contributor.author Sejberg, J en
dc.contributor.author Brimble, Margaret en
dc.date.accessioned 2011-09-19T03:43:44Z en
dc.date.issued 2008 en
dc.identifier.citation Org Biomol Chem 6(22):4261-4270 21 Nov 2008 en
dc.identifier.issn 1477-0520 en
dc.identifier.uri http://hdl.handle.net/2292/8104 en
dc.description.abstract The enantioselective synthesis of a dimeric pyranonaphthoquinone closely related to the cardinalins is described. Whilst attempts to effect a double Hauser–Kraus annulation of enone5 were unsuccessful using both bis-phthalide 4 and bis-sulfone21, a single annulation of cyanophthalide28 with enone5 furnished functionalised naphthalene31. Suzuki–Miyaura homocoupling of the aryl triflate 29 derived from 31 effected a late-stage construction of the biaryl bond and facilitated access to the biaryl 3. Double stereoselective lactolreduction installed the 1,3-cis stereochemistry of the pyran rings and a final double oxidative demethylation step furnished model dimer 1, completing the enantioselective synthesis of a dimeric pyranonaphthoquinone bearing the core structure of cardinalin 3. en
dc.language EN en
dc.publisher ROYAL SOC CHEMISTRY en
dc.relation.ispartofseries Organic & Biomolecular 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/1477-0520/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject CRISAMICIN-A en
dc.subject ANNULATION en
dc.subject ANION en
dc.subject NAPHTHOQUINONE en
dc.subject ANTIBIOTICS en
dc.subject DERIVATIVES en
dc.subject INHIBITOR en
dc.subject PALLADIUM en
dc.title Enantioselective Synthesis of the Dimeric Pyranonaphthoquinone Core of the Cardinalins Using a Late-Stage Homocoupling Strategy en
dc.type Journal Article en
dc.identifier.doi 10.1039/b813605j en
pubs.issue 22 en
pubs.begin-page 4261 en
pubs.volume 6 en
dc.rights.holder Copyright: 2008 Royal Society of Chemistry en
dc.identifier.pmid 18972059 en
pubs.end-page 4270 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 80847 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 18972059 en

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