SCHEDULED MAINTENANCE
An 18-hydroxypregnan-20-one, in the 20-hemiacetal form (II), reacts with lead tetra-acetate or with sources of electrophilic bromine to introduce acetoxy- or bromo-substituents, respectively, at C-21: alkaline hydrolysis then gives the 21-hydroxy-derivative in good overall yield.
D. N. Kirk and M. S. Rajagopalan, J. Chem. Soc., Chem. Commun., 1974, 145 DOI: 10.1039/C39740000145
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