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Communication | Regular issue | Vol 32, No. 4, 1991, pp.663-668
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5671
Synthetic Applications of 2-(1,3-Dithian-2-yl)indoles. III. A New Route to Tetracyclic [ABCD] Intermediates in the Synthesis of Aspidosperma Indole Alkaloids

Yves Troin, Anna Diez, Jean-Luc Bettiol, Mario Rubiralta,* David S. Grierson, and Henri-Phillippe Husson

*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain

Abstract

The synthesis of tetracyclic [ABCD] framework of Aspidosperma alkaloids has been achieved via allylamine-enamine isomerization using (Ph3P)3RhCl in hot aqueous acetonitrile of the 1,2,5,6-tetrahydro-3-(indolylethyl)pyridine (13) which in turn was obtained by Raney nickel desulfurization of the corresponding 2-(1,3-dithia-2-yl)indole (5a).