Synthesis of 18,21-dihydroxypregn-4-ene-3,20-dione (‘18-hydroxy-deoxycorticosterone’)

Abstract
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.

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