Synthetic steroids. Part II. The deconjugation of Δ4-3-oxo-steroids. An improved method for the preparation of 3β-hydroxyandrost-5-ene-11,17-dione
Abstract
Deconjugation of adrenosterone (I) and testosterone by the hydrolysis of their enol acetates and enamines, and by their reaction with strong base, has been studied. An improved synthesis of the 17-ethylene acetal of adrenosterone from its 3-mono-enamine is described, as is an improved route to 3β-hydroxyandrost-5-ene-11,17-dione (VIII) by the base deconjugation of 17-ethylenedioxyandrost-4-ene-3,11-dione (XVI).