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Bile acids. LXXXI. Synthesis and structural assignment of E/Z isomers of substituted methyl hydroxy-5
M N Iqbal1, P H Patrick, W H Elliott
1Edward A. Doisy Department of Biochemistry and Molecular Biology, St. Louis University School of Medicine, Missouri 63104.
Abstract:
Syntheses of the E and Z isomers of methyl 3 alpha-,3 alpha,7 alpha-,3 alpha,12 alpha-, and 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-oates are reported. Mass spectral studies show fragmentation patterns in support of assignment as the E or Z isomers, especially in differences in loss of the side chain. Chromatographic procedures, primarily gas chromatography and high-performance liquid chromatography, support these assignments. The E isomer predominates in either of two methods of synthesis.
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