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

Takumi Abe; Koji Yamada

doi:10.1021/acs.orglett.8b00330

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

Takumi Abe, Koji Yamada

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1469-1472
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.8b00330
Publication status	Published - Mar 2 2018
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b00330

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abstract = "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.",

author = "Takumi Abe and Koji Yamada",

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doi = "10.1021/acs.orglett.8b00330",

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AU - Abe, Takumi

AU - Yamada, Koji

N1 - Funding Information: This work was financially supported by JSPS KAKENHI Grant No. 16K18849 (T.A.) for Grant-in-Aid for Young Scientists (B). Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/3/2

Y1 - 2018/3/2

N2 - 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.

AB - 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.

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JO - Organic Letters

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

Abstract

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