Abstract
Hydrolysis by malt enzyme shows selectivity, as reported earlier, and this reaction is characterized by its progress under a very mild condition. This characteristic was utilized for the preparation of acid- and alkali-labile 16β-hydroxylated Reichstein's substance S (IV) and its 16-acetate (III), from its 16, 21-diacetate. (IV) undergoes rapid isomerization to 16α-hydroxylated substance S (V). Oxidation of (III) with sodium bismuthate gives 16β-acetoxyandrost-4-ene-3, 17-dione (VI) whose treatment with sulfuric acid or potassium hydroxide produces 16-oxotestosterone (VII).
