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Judicious application of the Prelog-Cram rule allowed the stereoselective synthesis of the title compounds. The 20β-hydroxy compound was prepared by the reaction of isohexylmagnesium bromide on 3β,17α-dihydroxy-5-en-20-one, while the 20α-hydroxy compound was prepared by the reaction of methylmagnesium bromide with 3β,17α-dihydroxy-21-norcholest-5-en-20-one. The preparation of the starting material and chemical and spectral arguments employed in the assignments of structure and stereochemistry will be discussed.
