A concise, stereoselective synthesis of (±)-geissoschizine

Article abstract of DOI:10.1016/S0040-4039(96)02097-7

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.