The Journal of Organic Chemistry

Stereoselective synthesis of (.+-.)-3, 4, 4a, 5, 6, 7, 8, 8a-octahydronaphthalen-1 (2H)-ones via homogeneous hydrogenation of (.+-.)-5, 6, 7, 8- …

JTA Reuvers, A De Groot

Index: Reuvers, Jack T. A.; Groot, Aede de Journal of Organic Chemistry, 1984 , vol. 49, p. 1110 - 1113

Full Text: HTML

Citation Number: 12

Abstract

Starting from ketones 5as and 5c, 8 the dienones 7a and 7c were prepared as described in Scheme I. 9 When these compounds were hydrogenated with Wilkinson's catalyst at 28 psi, the desired trans-fused bicyclic ketones la and IC were isolated in about 80% yield. Small quantities (45%) of partly hydrogenated products were formed, and no cis-fused reduction products could be detected. Hydrogenation of 5c with Pd/C gave 1: l mixtures of cis-and ...