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Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis






Chemistry and Physics of Lipids 178: 45-51

Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis

Mild and regioselective conversion of 3-keto-5α- and 3-keto-5β-steroids (trans A/B- and cis A/B-ring juncture, respectively) to the corresponding enones (Δ(1)- and Δ(4)-3-ketones) by treatment with o-iodoxybenzoic acid (IBX) catalyzed by trifluoroacetic acid (TFA) in DMSO, is described. The IBX-mediated reaction involved dehydrogenation of the α- and β-hydrogen atoms of the 3-ketones to give the enones regioselectively in good isolated yields without concomitant formation of related dienones and trienones.


Accession: 055445613

PMID: 24309193

DOI: 10.1016/j.chemphyslip.2013.11.007



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