Synthesis of the Tetracyclic Cores of the Integrastatins, Epicoccolide A and Epicocconigrone A.

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dc.contributor.author Jeong, Joo Young en
dc.contributor.author Sperry, Jonathan en
dc.contributor.author Brimble, Margaret en
dc.date.accessioned 2019-10-21T02:30:59Z en
dc.date.issued 2019-09 en
dc.identifier.issn 0022-3263 en
dc.identifier.uri http://hdl.handle.net/2292/48582 en
dc.description.abstract The integrastatins, epicoccolide A and epicoccongirone A, are natural products containing a unique [6.6.6.6]-tetracyclic core framework that exhibit a broad spectrum of biological activities. A synthesis of the common core of epicoccolide A and epicocconigrone A has been achieved using an umpolung alkylation-lactonization to assemble an isochromanone from which the bridged 1,3-dioxane was readily assembled. A different strategy was required to access the core on the integrastatins; an initial aryllithium addition to an aldehyde, followed by oxidation and treatment of the masked dihydroxyketone with acid gave the desired core structure. en
dc.format.medium Print-Electronic en
dc.language eng 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. en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject Heterocyclic Compounds, Bridged-Ring en
dc.subject Molecular Structure en
dc.subject Alkylation en
dc.subject Cyclization en
dc.subject Chemistry Techniques, Synthetic en
dc.title Synthesis of the Tetracyclic Cores of the Integrastatins, Epicoccolide A and Epicocconigrone A. en
dc.type Journal Article en
dc.identifier.doi 10.1021/acs.joc.9b01796 en
pubs.issue 18 en
pubs.begin-page 11935 en
pubs.volume 84 en
dc.rights.holder Copyright: The author en
pubs.end-page 11944 en
pubs.publication-status Published en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Research Support, Non-U.S. Gov't en
pubs.subtype Journal Article en
pubs.elements-id 779856 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 2019-08-17 en
pubs.dimensions-id 31416308 en


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