dc.contributor.author |
Lindsay, Ashley |
en |
dc.contributor.author |
Leung, Ka Ho Ivanhoe |
en |
dc.contributor.author |
Sperry, Jonathan |
en |
dc.date.accessioned |
2017-03-30T01:43:07Z |
en |
dc.date.issued |
2016-10-05 |
en |
dc.identifier.citation |
Organic Letters 18(20):5404-5407 05 Oct 2016 |
en |
dc.identifier.issn |
1523-7060 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/32379 |
en |
dc.description.abstract |
The total synthesis of the azepinobisindole alkaloid iheyamine A is described. The successful strategy hinged on an intermolecular cross-Mannich reaction between 5-methoxy-3-acetoxyindole and a protected tryptamine to access an unsymmetrical 2,2′-bisindole, which was subsequently converted into iheyamine A via a deep-blue 3-indolone intermediate. VT 1H NMR infers that iheyamine A exists as a mixture of tautomers that undergo intermediate chemical exchange on the NMR time scale. The intermolecular cross-Mannich reaction described herein is a viable alternative to metal-catalyzed cross-coupling strategies commonly employed to access 2,2′-bisindoles. |
en |
dc.publisher |
American Chemical Society |
en |
dc.relation.ispartofseries |
Organic Letters |
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.title |
Synthesis of the Azepinobisindole Alkaloid Iheyamine A Enabled by a Cross-Mannich Reaction |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1021/acs.orglett.6b02798 |
en |
pubs.issue |
20 |
en |
pubs.begin-page |
5404 |
en |
pubs.volume |
18 |
en |
dc.rights.holder |
Copyright: American Chemical Society |
en |
dc.identifier.pmid |
27704854 |
en |
pubs.end-page |
5407 |
en |
pubs.publication-status |
Published |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
542838 |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Chemistry |
en |
dc.identifier.eissn |
1523-7052 |
en |
pubs.record-created-at-source-date |
2017-03-30 |
en |
pubs.dimensions-id |
27704854 |
en |