Collect. Czech. Chem. Commun. 1989, 54, 1028-1035


Ladislav Kohout

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Acetolysis and hydrogenolysis of 7-methanesulfonyloxy-3α,5-cyclo-5α-cholestanes was studied. The 7β-methanesulfonyloxy derivative VI is hydrogenolyzed more readily than its 7α-isomer III. The acetolysis gives products of elimination, substitution and rearrangement with participation of the cyclopropane ring. Whereas the 7α-derivative III predominantly reacts with elimination, the 7β-derivative VI is more susceptible to the participation reaction.