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

作者：Viviano Posadas Alejandro O; Flores Alamo Marcos; Iglesias Arteaga Martin A^*

来源：Steroids, 2016, 113: 22-28.

DOI：10.1016/j.steroids.2016.06.003

• 3-Oxo-5 beta-steroids
• Hypervalent iodine
• Favorskii rearrangement
• Semi-benzylic mechanism
• NMR
• X-ray Diffraction

Treatment of 3-oxo-5 beta-steroids with diacetoxyiodobenzene/KOH triggered a fast and regioselective Favorskii rearrangement that exclusively led to 3 beta-methoxycarbonyl-5 beta-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-5 beta-steroids, only the last participates. Unambiguous characterization of the products was achieved by NMR and X-ray Diffraction studies.

• 出版日期2016-9