THE SYNTHESIS OF 3-BETA-(2-HYDROXYETHOXY) -5-ALPHA-CHOLEST-8(14)-EN-15-ONE AND ROXY-2-[H-3]ETHOXY)-5-BETA-CHOLEST-8(14)-EN-15-ONE

3 beta-(2-Hydroxyethoxy)-5 alpha-cholest-8(14)-en-15-one, a novel inhi bitor of cholesterol biosynthesis, was synthesized by a scheme involvi ng O-alkylation of the starting 3 beta-hydroxy-5 alpha-cholesta-7,14-d iene with triphenylmethoxyethyl toluenesulphonate, selective alpha-epo xidation of 14,15-double bond, and the rearrangement of the epoxide ob tained into the target product in an acidic medium. The alkylation of the 3 beta-hydroxy-5 alpha-cholesta-7,14-diene with 1-O-tosyl-2,3-isop ropylidene-sn-glycerol, the protective isopropylidene group removal, t he periodate oxidation of the diol formed the reduction of the interme diate aldehyde with sodium boro[H-3]hydride, 14,15 alpha-epoxidation o f the 3 beta-(2-hydroxy-2-[H-3]ethoxy)-5 alpha-cholesta-7,14-diene obt ained, and an acidic treatment of the intermediate epoxide yielded the desired 3 beta-(2-hydroxy-2-[H-3]ethoxy)-5 alpha-cholest-8(14)-ene-15 -one.