New synthesis of 2 beta-hydroxy-19-oxoandrost-4-ene-3,17-dione and its 2 beta-18O analog.
Treatment of 19-[oxygenated]-androst-4-ene-3,17-dione with Mn(AcO)3 and ClCH2COOH in benzene gave epimeric mixtures of the corresponding 2 zeta-chloroacetates and 2 zeta-acetates. The products were processed to give the title compound. For the synthesis of the 2-18O analog, ClCH2C18OOH was used, which was prepared from ClCH2COCl.
Worcester Foundation for Experimental Biology, Shrewsbury, MA 01545.
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Dharmaratne
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Shackleton
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Roitman
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Caspi
D000737:Androstenols / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D010103:Oxygen Isotopes
D000737:Androstenols; D010103:Oxygen Isotopes; C008064:2-beta-hydroxy-19-oxo-4-androstene-3,17-dione