Synthetic investigation on the building of ring A of steroids

Methyl 7-keto-1,2,3,4,4a,5,6,7-octahydronaphthoate (Va) has been prepared by the reduction of 7-methoxy-1,2,3,4-tetrahydronaphthoic acid (III) with lithium and ammonia followed by hydrolysis of the enol ether, esterification and migration of the double bond. Alkylation of Va has led to the substitution at the expected 8-position. Methyl 4-keto-7-methoxy-1,2,3,4-tetrahydronaphthoate (X), an intermediate in the preparation of III, has been converted into methyl 3-methyl-3-cyano-4-keto-7-methoxy-1,2,3,4-tetrahydronaphthoate (XIII).