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 |
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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 |
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dc.subject |
Molecular Structure |
en |
dc.subject |
Alkylation |
en |
dc.subject |
Cyclization |
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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 |