期刊
ORGANIC LETTERS
卷 18, 期 20, 页码 5404-5407出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02798
关键词
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资金
- University of Auckland
- Royal Society of New Zealand
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 H-1 NMR infers that iheyamine A exists as a mixture of tautomers that undergo intermediate chernical 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.
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