Practical synthesis of androgen: the efficient transformation of 17-oxo group to 17 alpha-hydroxy group.
The present report describes the improved transformation of the 17-oxo group in 3 beta-acetoxy-5 alpha-androstan-17-one to a 17 alpha-hydroxy group. A mixture of 17 alpha-acetoxy and 16-ene compounds, which are usually produced by the standard synthetic route, were treated with peracetic acid (epoxidation of the 16-ene compound) and then sodium borohydride-sodium hydroxide (reduction-hydrolysis) to give the desired 17 alpha-hydroxy compound in much better yield than that in previous reports. Recrystallization of the crude product with cyclohexane-methanol gave the pure compound in 54% yield (total yield from starting ketone).
Ohta
T
T
Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyoto, Japan.
Zhang
H
H
Torihara
Y
Y
Hida
T
T
Furukawa
I
I
D000728:Androgens / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000728:Androgens