The hydroxylation of cholest-4-en-7β-ol

Abstract

Hydroxylation of cholest-4-en-7β-ol with osmium tetroxide gives principally 4β,5,7β-trihydroxy-5β-cholestane accompanied by some 4α,5,7β-trihydroxy-5α-cholestane, whereas peracids give mainly 4β,5,7β-trihydroxy-5α-cholestane and a little 4α,5,7β-trihydroxy-5β-cholestane. The four triols were related by oxidation to the corresponding 5-hydroxy-4,7-diketones and the orientation at C-5 was established by optical rotatory dispersion and elimination studies.