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Dehydrative Mannich-Type Reaction for the Synthesis of Azepinobisindole Alkaloid Iheyamine A

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journal contribution
posted on 13.02.2018, 14:06 by Takumi Abe, Koji Yamada
A concise synthesis of the azepinobisindole alkaloid iheyamine A from an indole-2,3-epoxide equivalent has been achieved. This method features a formal C3 electrophilic reaction of an indole-2,3-epoxide equivalent with tryptamine to form a 3-aminoindoline and a novel In-catalyzed dehydrative Mannich-type reaction of the hemiaminal to give the azepinobisindole core.