Potential bile acid metabolites. 17. Synthesis of 2 beta-hydroxylated bile acids |
| |
Authors: | T Iida I Komatsubara F C Chang J Goto T Nambara |
| |
Institution: | College of Engineering, Nihon University, Fukushima-ken, Japan. |
| |
Abstract: | 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. |
| |
Keywords: | |
|
|