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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.