Synthesis of (19E)-17β-hydroxy-3-oxoandrost-4-en-19-al 19-(O-carboxymethyl)oxime

Abstract

The title compound XIII was synthesized from epoxide I. Cleavage with zinc dust and Jones' oxidation under mild conditions afforded aldehyde V. Reaction with (O-carboxymethyl)hydroxylamine hemihydrochloride followed by methylation with diazomethane led to oxime X which on partial hydrolysis gave the 3-hydroxy derivative VIII. Its oxidation accompanied with a rearrangement of the double bond yielded ketone XVI which on hydrolysis afforded the desired hapten XIII.