Synthesis of the Azepinobisindole Alkaloid Iheyamine A Enabled by a Cross-Mannich Reaction

Show simple item record Lindsay, Ashley en Leung, Ka Ho Ivanhoe en Sperry, Jonathan en 2017-03-30T01:43:07Z en 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 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 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 en
pubs.subtype Article en
pubs.elements-id 542838 en Science en Chemistry en
dc.identifier.eissn 1523-7052 en
pubs.record-created-at-source-date 2017-03-30 en
pubs.dimensions-id 27704854 en

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