Synthetic applications of 2-cyanopiperidines. Model studies in the synthesis of bridged indole alkaloids

J Bosch, M Feliz, ML Bennasar

Index: Bosch, Joan; Feliz, Miguel; Bennasar, M.-Lluisa Tetrahedron, 1984 , vol. 40, # 8 p. 1419 - 1424

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Citation Number: 14

Abstract

Acid cyclization of 4-(indol-1-and-3-ylmethyl)-2-cyanopiperidines 5̃ led to the bridged tetracyclic indole-systems 1̃ and 2̃. The required 2-cyanopiperidines 5̃ were prepared by catalytic hydrogenation of 2-cyano-1, 2, 3, 6-tetrahydropyridines 4̃ and by DIBAL reduction of lactams 7̃ followed by cyanide ion addition to the intermediate enamine.