Potential bile acid metabolites. 13. Improved routes to 3p,6p- and 3P,6~di hydroxy=5~-cholanoic acids'

New synthetic routes to three possible stereoisomers of hyodeoxycholic (3a,6a-dihydroxy-5~-cholanic) acid are de- scribed. The principal reactions involved were inversion at C-3 of 3a-hydroxy-6-oxo derivatives with diethyl azodicarboxylate- triphenylphosphine-formic acid and with N,N-dimethylforma- mide, without allomerization to the more stable 5a form. On the basis of physical and chromatographic data, previously reported 3P,6a-dihydroxy-5P-cholanic acid and its methyl ester are shown to be C-3 epimeric mixtures. The ''C nuclear magnetic resonance spectra were of key importance in characterizing the stereoisomers and estimating their purity. - Iida, T., T. Momose,

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