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Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B. 2021
Takashi Nishiyama, and
Erina Hamada, and
Daishi Ishii, and
Yuuto Kihara, and
Nanase Choshi, and
Natsumi Nakanishi, and
Mari Murakami, and
Kimiko Taninaka, and
Noriyuki Hatae, and
Tominari Choshi
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan.
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.
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