The first total synthesis of 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.
Keywords: pyrrolo[2,3-c]quinoline; trigonoine B; electrocyclization; 2-azahexatiriene system; carbodiimide
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Nishiyama, T.; Hamada, E.; Ishii, D.; Kihara, Y.; Choshi, N.; Nakanishi, N.; Murakami, M.; Taninaka, K.; Hatae, N.; Choshi, T. Beilstein Arch. 2021, 20216. doi:10.3762/bxiv.2021.6.v1
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