J. Lipid Res. Acyl Labeled PIP's available August 1, 2008
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Journal of Lipid Research, Vol 29, 165-171, Copyright © 1988 by Lipid Research, Inc.

ARTICLES

Potential bile acid metabolites. 13. Improved routes to 3 beta, 6 beta- and 3 beta, 6 alpha-dihydroxy-5 beta-cholanoic acids

T Iida, T Momose, T Tamura, T Matsumoto, FC Chang, J Goto and T Nambara
College of Engineering, Nihon University, Fukushima-ken, Japan.

New synthetic routes to three possible stereoisomers of hyodeoxycholic (3 alpha, 6 alpha-dihydroxy-5 beta-cholanic) acid are described. The principal reactions involved were inversion at C-3 of 3 alpha-hydroxy-6- oxo derivatives with diethyl azodicarboxylate-triphenylphosphine-formic acid and with N,N-dimethylformamide, without allomerization to the more stable 5 alpha form. On the basis of physical and chromatographic data, previously reported 3 beta, 6 alpha-dihydroxy-5 beta-cholanic acid and its methyl ester are shown to be C-3 epimeric mixtures. The 13C nuclear magnetic resonance spectra were of key importance in characterizing the stereoisomers and estimating their purity.
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