Synthesis of 19-hydroxy-[7-2H2]androstenedione for human metabolism studies

19-Hydroxyandrostenedione (19-OHA), highly labeled with deuterium at position 7, was synthesized from unlabeled androstenediol diacetate. The deuterium labels were introduced into the 7-keto compound with dichloroaluminum deuteride to obtain 7-2H2]androstenediol. The labeled androstenediol diacetate was converted to the labeled 19-OHA by a five-step sequence without appreciable loss of deuterium. The labeled 19-OHA is useful as an internal standard for gas chromatography-mass spectroscopy analysis of the endogenous levels and as a tracer for in vivo metabolic studies.