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Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B.

ABSTRACT: The first total synthesis of the pyrrolo[2,3-c]quinoline alkaloid trigonoine B (1) was accomplished via a six-step sequence involving the construction of an N-substituted 4-aminopyrrolo[2,3-c]quinoline framework via electrocyclization of 2-(pyrrol-3-yl)benzene containing a carbodiimide moiety as a 2-azahexatriene system. The employed six-step sequence afforded trigonoine B (1) in 9.2% overall yield. The described route could be employed for the preparation of various N-substituted 4-aminopyrroloquinolines with various biological activities.

SUBMITTER: Nishiyama T

PROVIDER: S-EPMC7991618 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B.

Nishiyama Takashi T Hamada Erina E Ishii Daishi D Kihara Yuuto Y Choshi Nanase N Nakanishi Natsumi N Murakami Mari M Taninaka Kimiko K Hatae Noriyuki N Choshi Tominari T

Beilstein journal of organic chemistry 20210316

The first total synthesis of the pyrrolo[2,3-c]quinoline alkaloid trigonoine B (1) was accomplished via a six-step sequence involving the construction of an N-substituted 4-aminopyrrolo[2,3-c]quinoline framework via electrocyclization of 2-(pyrrol-3-yl)benzene containing a carbodiimide moiety as a 2-azahexatriene system. The employed six-step sequence afforded trigonoine B (1) in 9.2% overall yield. The described route could be employed for the preparation of v ...[more]

PMID: 33796160

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