title: Regioselective oxidation of cholic acid and its 7β epimer by using o-iodoxybenzoic acid.
abstract: Rational exploration directed by DFT (density functional theory) based atomic Fukui indices, lead to development of regioselective oxidation of cholic acid and its 7β epimer by o-iodoxybenzoic acid. In case of cholic acid only, 7α-hydroxyl underwent oxidation, where as in its 7β epimer the selectivity was towards 12α-hydroxy group. Since these oxidations are the key steps in synthesis of ursodeoxycholic acid starting from cholic acid these findings may be useful in devising a protection free synthetic route.
authors.affiliation: Department of Pharmaceutical Sciences & Technology, Institute of Chemical Technology, Matunga, Mumbai 400019, India.
authors.forename: Prasad S
authors.initials: PS
authors.lastname: Dangate
authors.forename: Chetan L
authors.initials: CL
authors.lastname: Salunke
authors.forename: Krishnacharya G
authors.initials: KG
authors.lastname: Akamanchi
mesh_terms: D019826:Cholic Acid / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014580:Ursodeoxycholic Acid / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D007462:Iodobenzenes; C476101:o-iodoxybenzoic acid; D014580:Ursodeoxycholic Acid; D019826:Cholic Acid