A stereocontrolled synthesis of (+/-)-geissoschizine, involving the addition of the enolate derived from 1-acetylindole to pyridinium salt 2, cyclization of the resultant 1,4-dihydropyridine stereoselective elaboration of the E-ethylidene substituent, closure of C ring by Pummerer reaction, and methanolysis of the resulting pentacyclic lactam, is reported. Copyright (C) 1996 Elsevier Science Ltd