Potential bile acid metabolites. 17. Synthesis of 2 beta-hydroxylated bile acids.
The 2 beta-hydroxylated derivatives of lithocholic, chenodeoxycholic, deoxycholic, and cholic acids were synthesized from the respective parent bile acids by established procedures. The principal reactions involved were (1) bromination of 3-oxo formylated bile acids in N,N-dimethylformamide, (2) rearrangement and substitution of the resulting 4 beta-bromo-3-oxo derivatives to the 2 beta-acetoxy-3-oxo compounds with potassium acetate, and (3) reduction to the 2 beta-acetoxy-3 alpha-hydroxy compounds with tert-butylamine-borane complex. As for the prepared 2 beta-hydroxylated bile acids with a diequatorial trans-glycol structure, proton and carbon-13 nuclear magnetic resonance spectroscopic and gas-liquid chromatographic/mass spectrometric properties are discussed.
Iida
T
T
College of Engineering, Nihon University, Fukushima-ken, Japan.
Komatsubara
I
I
Chang
F C
FC
Goto
J
J
Nambara
T
T
D000085:Acetates; D019342:Acetic Acid; D055598:Chemical Phenomena; D002621:Chemistry; D002635:Chenodeoxycholic Acid / Q000031:analogs & derivatives; D019826:Cholic Acid; D002793:Cholic Acids / Q000737:chemistry; D003840:Deoxycholic Acid / Q000031:analogs & derivatives; D004126:Dimethylformamide; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D008095:Lithocholic Acid / Q000031:analogs & derivatives; D009682:Magnetic Resonance Spectroscopy
D000085:Acetates; D002793:Cholic Acids; D005227:Fatty Acids; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; D008095:Lithocholic Acid; D004126:Dimethylformamide; D019826:Cholic Acid; D019342:Acetic Acid