Process improvements in steroid chemistry

摘要

Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding alpha,beta-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the alpha,beta-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol using a hydroborating reagent followed by oxidative workup, e.g., borane followed by sodium perborate. Benzoyl and substituted benzoyls are superior protecting groups for hydroxyl groups present in the compounds.