Collect. Czech. Chem. Commun. 1990, 55, 2086-2094

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

Jan Fajkoša, Vladimír Pouzara and Karel Verešb

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Institute of Nuclear Biology and Radiochemistry, Czechoslovak Academy of Sciences, 142 20 Prague 4


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.