Abstract
ALTHOUGH the stereochemistry of the A and B rings of the sterols and allied substances has been very fully developed, the evidence for the stereo-chemical configurations of the other rings rests on less secure grounds. The evidence for the trans fusion of the B and C rings rests solely on the requirements of a flat molecule as adduced from X-ray data, while that for the trans fusion of rings C and D is based on the isolation of the tricarboxylic acid (I) by the step-wise degradation of 12-ketocholanic acid1 and desoxycholic acid2. This acid on pyrolysis gave an anhydride which on hydrolysis furnished an isomeric tricarboxylic acid. It was, therefore, deduced that the former acid had a trans configuration, from which it was assumed that the fusion of rings C and D was originally in the trans position. This conclusion would seem to be sound provided that no inversion occurred in the degradation, a loop-hole which cannot be excluded.
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References
Wieland and Dane, Z. pliysiol. Chem., 216, 91 (1933).
Wieland and Schlichting, Z. physiol Chem., 134, 276 (1924).
laucht, Z. physiol. Chem., 237, 236 (1935).
Reindel and Walter, Ann., 452, 45 (1927). Heilbron and Wilkinson, J. Chem. Soc., 1708 (1932).
Hart and Emerson, J. Amer. Chem. Soc., 54, 1073 (1932).
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PEAK, D. Stereochemistry of the Sterols and the Bile Acids. Nature 140, 280–281 (1937). https://doi.org/10.1038/140280b0
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DOI: https://doi.org/10.1038/140280b0
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