title: Allylic oxidation of steroidal olefins by vanadyl acetylacetonate and tert-butyl hydroperoxide.
abstract: Readily available vanadyl acetylacetonate was found to oxidize the allylic sites of Δ(5) steroidal alcohols without protection of hydroxyl groups. Cholesterol, dehydroepiandrosterone, cholesterol benzoate, cholesterol acetate, pregnenolone, and 5-pregnen-3,20-diene were oxidized to 7-keto products using vanadyl acetylacetonate in one pot reactions at room temperature in the presence of oxygen and water.
authors.affiliation: Department of Chemistry and Biochemistry, College of Science and Mathematics, Auburn University, Auburn, AL 36849-5319, United States.
authors.forename: Wendell S
authors.initials: WS
authors.lastname: Grainger
authors.affiliation: Department of Chemistry and Biochemistry, College of Science and Mathematics, Auburn University, Auburn, AL 36849-5319, United States. Electronic address: parisej@auburn.edu.
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Parish
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry; D006885:Hydroxybutyrates / Q000737:chemistry*; D010084:Oxidation-Reduction; D010422:Pentanones / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry*; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
chemical_list: D000475:Alkenes; D006885:Hydroxybutyrates; D010422:Pentanones; D013256:Steroids; C049529:acetyl acetonate; D020122:tert-Butylhydroperoxide; D001554:Benzene
keywords: 7-Ketocholesterol; Oxidation; Vanadyl acetylacetonate; tert-Butyl hydroperoxide