Synthesis of 19-hydroxy-androstenedione for human metabolism studies

Article abstract of DOI:10.1016/0039-128X(90)90066-K

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.