A new synthetic route to the indolo[2,3-a]quinolizidine system, involving the Pd(0)-catalyzed cross-coupling of a 2-indolylzinc derivative with a 2-halopyridine, stereoselective hydrogenation of the pyridine ring, and electrophilic cyclization upon the indole 3-position from the resulting 2-(2-piperidyl)indole, is reported. (C) 1996 Elsevier Science Ltd.