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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 11
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Original Articles

Potential Bile Acid Metabolites. 5.1 12B-Hydroxy Acids by Stereoselective Reduction

Pages 875-879 | Published online: 05 Dec 2006

References

  • lida , T. , Taneja , H. and Chang , F. C. J. Org. Chem. , Paper #4. submitted
  • Sorkin , M. and Reichstein , T. 1943 . Helv. Chim. Acta , 26 : 2097
  • Chang , F. C. , Wood , N. F. and Holton , W. G. 1965 . J. Org. Chem. , 30 : 1718
  • Chang , F. C. 1979 . J. Org. Chem. , 44 : 25
  • All the cholanic acid derivatives reported in this paper are of the 5β‐series; the 5β designation thus has been omitted. “Cholanic” is used instead of the IUPAC‐suggested name “cholanoic”
  • Andrews , G. C. and Crawford , T. C. 1980 . Tetrahedron Lett. , : 693
  • Reduction of the free acids proceeds equally well, but esters were used to facilitate HPLC analysis. Methylene chloride also is a satisfactory solvent as reported,” but methanol was chosen because of better solubility for our compounds
  • Rough deductions of the substituent effect on degree of stereoselectivity might be made on the basis of these results, especially in the case of the 12‐oxo reductions, but experiments carried out under more controlled analytical conditions are needed
  • Unpublished; report in preparation
  • Fieser , L. F. and Ettore , R. 1953 . J. Am. Chem. Soc. , 75 : 1700
  • Press , J. and Reichstein , T. 1942 . Helv. Chim. Acta , 25 : 878
  • Matschiner , J. T. 1971 . The Bile Acids , Edited by: Nair , P. P. and Kritchevsky , D. vol I , 17 N.Y. : Plenum Press .
  • Samulsson , B. 1960 . Acta Chem. Scand. , 14 : 17

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