Allylic oxidation of steroidal olefins by vanadyl acetylacetonate and tert-butyl hydroperoxide

Wendell S Grainger; Edward J Parish

doi:10.1016/j.steroids.2015.06.005

Allylic oxidation of steroidal olefins by vanadyl acetylacetonate and tert-butyl hydroperoxide

Steroids. 2015 Sep:101:103-9. doi: 10.1016/j.steroids.2015.06.005. Epub 2015 Jun 16.

Authors

Wendell S Grainger¹, Edward J Parish²

Affiliations

¹ Department of Chemistry and Biochemistry, College of Science and Mathematics, Auburn University, Auburn, AL 36849-5319, United States.
² Department of Chemistry and Biochemistry, College of Science and Mathematics, Auburn University, Auburn, AL 36849-5319, United States. Electronic address: parisej@auburn.edu.

PMID: 26091580
DOI: 10.1016/j.steroids.2015.06.005

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.

Keywords: 7-Ketocholesterol; Oxidation; Vanadyl acetylacetonate; tert-Butyl hydroperoxide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Benzene / chemistry
Hydroxybutyrates / chemistry*
Oxidation-Reduction
Pentanones / chemistry*
Steroids / chemistry*
tert-Butylhydroperoxide / chemistry*

Substances

Alkenes
Hydroxybutyrates
Pentanones
Steroids
acetyl acetonate
tert-Butylhydroperoxide
Benzene