Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds

An intermediate in the synthesis of squalamine or a homologous aminosterol having the structure:

• represents either a single or double bond;
• represents the location where the R10 or R12 moieties are bonded to the remainder of the steroid molecule;
• C1 to C6, each independently represents an alkyl, alkenyl, or alkynyl group, having 1 to 6 carbon atoms, wherein the group may be substituted or unsubstituted;
• and
• R13 and R14, each independently represents formyl;
• acetyl;
• propionyl;
• pivaloyl;
• cyanoacetyl;
• benzoyl;
• benzoyl ortho or para substituted with nitro, halogen, or alkoxy;
• methoxycarbonyl (methylcarbonate);
• ethoxycarbonyl;
• benzyloxycarbonyl;
• benzyl;
• benzyl ortho or para substituted with nitro;
• benzyl para substituted with a halogen;
• benzyl para substituted with a methoxy;
• benzyloxymethyl;
• benzyloxymethyl ortho or para substituted with nitro;
• benzyloxymethyl para substituted with a halogen;
• benzyloxymethyl para substituted with a methoxy;
• tetrahydrothiopyranyl;
• tetrahydrothiofuranyl;
• methylthiomethyl;
• trialkylsilyl, wherein each alkyl is independently selected from the group of methyl, ethyl, isopropyl, sec-butyl, tert-butyl, and phenyl;
• tetrahydropyranyl;
• 2-methoxyethoxymethyl;
• and methoxymethyl.