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Paper | Regular issue | Vol 29, No. 11, 1989, pp.2121-2133
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5114
Synthetic Applications of 2-(1,3-Dithian-2-yl)indoles. A New Synthetic Approach to Strychnos Alkaloids

Mario Rubiralta,* Antoni Torrens, Ignasi Reig, David S. Grierson, and Henri-Philippe Husson

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

Abstract

The first synthesis of Na-methyl-20-hydroxydasycarpidone 17b and the tetracyclic systems 16a and 16b are reported. The synthesis involves an acid cyclization of an appropriate 4-indolyl -carbonyl-2-piperidinecarbonitrile 15 which in turn is obtained
regioseiectively from the corresponding piperidinol 9 by a modified Polonovski reaction.