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Total Synthesis of Iheyamine A via the Cyanide-Catalyzed Imino-Stetter Reaction

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journal contribution
posted on 01.06.2020, 13:03 by Jiye Jeon, Hyung Joo Kim, Cheol-Hong Cheon
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.

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