Total Synthesis of Iheyamine A via the Cyanide-Catalyzed Imino-Stetter Reaction
- 19 June 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (12), 8149-8156
- https://doi.org/10.1021/acs.joc.0c01051
Abstract
The total synthesis of iheyamine A from readily available ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde is described. The cyanide-catalyzed imino-Stetter reaction of an aldimine derived from ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde provided the desired unsymmetrical 2,2'-bisindole-3-acetic acid derivative. The subsequent introduction of an amino group at the C-3' position, followed by the formation of the azepine ring, completed the total synthesis of iheyamine A.Funding Information
- National Research Foundation of Korea (NRF-2014-011165, NRF-2018R1D1A1A02086110, NRF-2020M2A8A4027369)
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