A Concise Approach for the Synthesis of the ABCD Ring System of Alpkinidine

A two step synthesis of a benzo analog of alpkinidine is described via Negishi coupling followed by a base mediated annulation reaction strategy. The organozinc compound prepared from ethyl 2-iodobenzoate was coupled with 4-chloro-2-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]quinolin-1-one to obtain ethyl 2-(2-methyl-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]quinolin-4-yl)-benzoate which on further treatment with a base provided ABCD ring system of alpkinidine. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim