Conversion of cholic acid to methyl 3alpha-carbethoxy-12alpha-acetoxy-6-oxo-5beta-chol-7-en-24-oate

A new and efficient method for preparation of a 7-en-6-one derivative of cholic acid is described. Acetylation of the known methyl 3alpha-carbethoxy-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate (3) at 12 position and reduction of its 7-oxo group yield the 12alpha-acetoxy-7alpha-hydroxy derivative 5. D...

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Bibliographic Details
Published inSteroids Vol. 68; no. 3; pp. 253 - 256
Main Authors Masterson, Sean P, Miller, Thomas A, Nassim, Bahman E
Format Journal Article
LanguageEnglish
Published United States 01.03.2003
Subjects
Chemistry, Organic - methods
Cholic Acid - chemistry
Cholic Acid - metabolism
Cholic Acids - chemistry
Cholic Acids - metabolism
Spectrum Analysis
Stereoisomerism
X-Ray Diffraction
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Summary:A new and efficient method for preparation of a 7-en-6-one derivative of cholic acid is described. Acetylation of the known methyl 3alpha-carbethoxy-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate (3) at 12 position and reduction of its 7-oxo group yield the 12alpha-acetoxy-7alpha-hydroxy derivative 5. Dehydration of the 7alpha-hydroxy group in 5 followed by allylic oxidation provide methyl 3alpha-carbethoxy-12alpha-acetoxy-6-oxo-5beta-chol-7-en-24-oate (7) in good yield.
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ISSN:0039-128X