Synthesis of 5 alpha-androstane-3 alpha, 16 alpha, 17 beta-triol from 3 beta-hydroxy-5-androsten-17-one.
5 alpha-Androstane-3 alpha, 16 alpha, 17 beta-triol was synthesized from 3 beta-hydroxy-5-androsten-17-one. The procedure involved catalytic hydrogenation of 3 beta-hydroxy-5-androsten-17-one to 3 beta-hydroxy-5 alpha-androstan-17-one. This was followed by conversion of the 3 beta-hydroxy group to 3 alpha-benzoyloxy group by the Mitsunobu reaction. Further treatment with isopropenyl acetate yielded 5 alpha-androsten-16-ene-3 alpha, 17-diol 3-benzoate 17-acetate. This was then converted to 3 alpha, 17-dihydroxy-5 alpha-androstan-16-one 3-benzoate 17-acetate via the unstable epoxide intermediate after treatment with m-cloroperoxybenzoic acid. LiA1H4 reduction of this compound formed 5 alpha-androstane-3 alpha, 16 alpha, 17 beta-triol. 1H and 13C NMR of various steroids are presented to confirm the structure of this compound.
D015113:Androstane-3,17-diol / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000732:Androstanols / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D000732:Androstanols; D007202:Indicators and Reagents; D015113:Androstane-3,17-diol; C031484:androstane-2,3,17-triol