dc.contributor.author |
Ding, Xiaobo |
en |
dc.contributor.author |
Furkert, Daniel |
en |
dc.contributor.author |
Brimble, Margaret |
en |
dc.date.accessioned |
2018-11-13T23:28:59Z |
en |
dc.date.issued |
2016-10 |
en |
dc.identifier.issn |
1359-7345 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/44225 |
en |
dc.description.abstract |
The heronapyrroles are a family of antibiotic natural products containing the rare 2-nitropyrrole motif. We report here a second generation total synthesis that circumvents problems of selective pyrrole nitration and alkene formation that limited the utility of previous approaches. Stille sp3-sp2 cross coupling of a novel 2-nitropyrrole fragment was developed to install the key C7,8 olefin with complete regiochemical control. An unusual Hunsdiecker-type decarboxylative halogenation was also identified, providing access to the complex vinyl stannane coupling partners required for formation of the natural product. |
en |
dc.format.medium |
Print |
en |
dc.language |
eng |
en |
dc.relation.ispartofseries |
Chemical communications (Cambridge, England) |
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 |
Streptomyces |
en |
dc.subject |
Pyrroles |
en |
dc.subject |
Biological Products |
en |
dc.subject |
Anti-Bacterial Agents |
en |
dc.subject |
Molecular Structure |
en |
dc.subject |
Stereoisomerism |
en |
dc.title |
2-Nitropyrrole cross-coupling enables a second generation synthesis of the heronapyrrole antibiotic natural product family. |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1039/c6cc07532k |
en |
pubs.issue |
85 |
en |
pubs.begin-page |
12638 |
en |
pubs.volume |
52 |
en |
dc.rights.holder |
Copyright: The author |
en |
dc.identifier.pmid |
27722263 |
en |
pubs.end-page |
12641 |
en |
pubs.publication-status |
Published |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Journal Article |
en |
pubs.elements-id |
542795 |
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 |
1364-548X |
en |
pubs.record-created-at-source-date |
2016-10-11 |
en |
pubs.dimensions-id |
27722263 |
en |