Synthesis of Deuterium-Labeled 16α, 19-Dihydroxy C_<19> Steroids as Internal Standards for Gas Chromatography-Mass Spectrometry

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[2β, 7,7,16β-^2H_4]16α, 19-Dihydroxyandrost-4-ene-3,17-dione (14) and [7,7,16β-^2H_3]3β, 16α, 19-trihydroxyandrost-5-en-17-one (16), with high isotopic purity, respectively, were synthesized from unlabeled 3β-(tert-butyldimethylsiloxy)-androst-5-ene-17β-yl acetate (1). The deuterium introduction at C-7 was carried out by reductive deoxygenation of the 7-keto compound 3 with dichloroaluminum deuteride and that at C-2β and/or C-16β by controlled alkaline hydrolysis of 16-bromo-17-ketone 11 or 12 with NaOD in D_2O and pyridine. [7,7-^2H_2]3β-Hydroxyandrost-5-en-17-one (6), obtained from compound 1 by a five-step sequence, was converted to compound 14 or 16 by an eight-step or seven-step sequence, respectively. The labeled steroids 14 and 16 are useful as internal standards for gas chromatography-mass spectrometry analysis of the endogeneous levels.
公益社団法人日本薬学会の論文
1992-10-25