Journal of Lipid Research, Vol 32, 649-658, Copyright © 1991 by Lipid Research, Inc.
Potential bile acid metabolites. XVIII. Synthesis of stereoisomeric 3,6,12 alpha-trihydroxy-5 beta-cholanoic acids
T Iida, T Tamaru, FC Chang, J Goto and T Nambara
College of Engineering, Nihon University, Fukushima-ken, Japan.
Two new 6-hydroxylated bile acids, 3 beta, 6 alpha, 12 alpha- and 3 beta, 6
beta, 12 alpha-trihydroxy-5 beta-cholanoic acids, were synthesized from
deoxycholic acid. In addition, their C-3 epimers, 3 alpha, 6 alpha, 12
alpha- and 3 alpha, 6 beta, 12 alpha-trihydroxy acids, were prepared by a
new route. The principal reactions used were 1) 6 beta-hydroxylation of
3-methoxy-3,5-dienes with m-chloroperbenzoic acid in aqueous dioxane; 2)
catalytic hydrogenation of the resulting 6 beta-hydroxy-3-oxo-4-enes to the
6 beta-hydroxy-3-oxo-5 beta compounds with palladium on calcium carbonate
catalyst in ethanol; and 3) stereoselective reduction of appropriate 3-oxo
derivatives with potassium tri-sec-butylborohydride and
tert-butylamine-borane complex. The thin-layer chromatographic, gas-liquid
chromatographic, and high performance liquid chromatographic mobilities,
and 1H- and 13C-nuclear magnetic resonance spectroscopic data of the four
stereoisomers are presented. With this work all the 6-hydroxylated
derivatives of lithocholic, deoxycholic, chenodeoxycholic, ursodeoxycholic,
and cholic acids in the 5 beta series are now known and have been
synthesized.
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