Regioselective hypervalent iodine-induced Favorskii rearrangement of 3-oxo-5β-steroids

    loading  Checking for direct PDF access through Ovid

Abstract

Treatment of 3-oxo-5β-steroids with diacetoxyiodobenzene/KOH triggered a fast and regioselective Favorskii rearrangement that exclusively led to 3β-methoxycarbonyl-5β-4-norsteroids in good yields. The outcome of the reaction indicates that although both Cyclopropanone and Semi-benzylic pathways are possible, in the case of 3-oxo-5β-steroids, only the last participates. Unambiguous characterization of the products was achieved by NMR and X-ray Diffraction studies.

Related Topics

    loading  Loading Related Articles