Collection of Czechoslovak Chemical Communications - digital archive 

Abstract

Action of some nucleophilic reagents (CH₃COOAg, CH₃COOK, LiAlH₄) on 6β-chloro- and 6β-methanesulfonyloxy-5-methyl-19-nor-5β-cholest-9-enes VIII - XII affords predominantly A-homo-B,19-dinor-5β-cholest-9-ene derivatives, arising by rearrangement and substitution (XIII, XXIV) or rearrangement and elimination (e.g. XX). Hydrogenolysis of compounds of the type VIII with lithium aluminium hydride gives, in addition, a product of rearrangement, fragmentation and further reduction (XXVI), and 5-methyl-6α,10-cyclo-19-nor-5β,9β,10α-cholestan-3β-ol (XXX).