Abstract
Abstract The effects of C11-substituents on the hydroxylation of Δ1,4-3-oxosteroids with osmium tetroxide, have been examined. The 11α-substituents, such as 11α-hydroxy, 1α-acetoxy or 11α-methyl-11β-hydroxy groups, result in the selective addition of osmium tetroxide at the Δ4 double bond, giving 4β,5β-dihydroxy-Δ1-3-oxosteroids. On the other hand, the 11-oxo yields exclusively 1α,2α-dihydroxy-Δ4-3-oxosteroids. Oxidation of the 1α,2α-dihydroxy-Δ4-3-oxosteroids having the 11-oxo group with manganese dioxide yields the corresponding A-nor-Δ3(5)-1,2-dioxosteroids, which, however, tend to form the hydrate at the C1-oxo group.
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