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 |