title: Conversion of cholic acid to methyl 3alpha-carbethoxy-12alpha-acetoxy-6-oxo-5beta-chol-7-en-24-oate.
abstract: 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.
authors.affiliation: Department of Chemistry, Indiana University Southeast, 4201 Grant Line Road, New Albany, IN 47150, USA.
authors.forename: Sean P
authors.initials: SP
authors.lastname: Masterson
authors.forename: Thomas A
authors.initials: TA
authors.lastname: Miller
authors.forename: Bahman E
authors.initials: BE
authors.lastname: Nassim
mesh_terms: D002625:Chemistry, Organic / Q000379:methods; D019826:Cholic Acid / Q000737:chemistry / Q000378:metabolism*; D002793:Cholic Acids / Q000737:chemistry / Q000378:metabolism*; D013057:Spectrum Analysis; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D002793:Cholic Acids; C479599:methyl 3-carbethoxy-12-acetoxy-6-oxochol-7-en-24-oate; D019826:Cholic Acid