区域选择性高价碘诱导的3-氧代-5β-甾体的法沃斯基重排反应
Regioselective hypervalent iodine-induced Favorskii rearrangement of 3-oxo-5β-steroids.
作者信息
Viviano-Posadas Alejandro O, Flores-Álamo Marcos, Iglesias-Arteaga Martín A
机构信息
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico.
Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510 México, D.F., Mexico.
出版信息
Steroids. 2016 Sep;113:22-8. doi: 10.1016/j.steroids.2016.06.003. Epub 2016 Jun 7.
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.
用二乙酰氧基碘苯/氢氧化钾处理3-氧代-5β-甾体引发了快速且区域选择性的法沃斯基重排反应，该反应专一性地生成了产率良好的3β-甲氧基羰基-5β-4-降甾体。反应结果表明，尽管环丙酮和半苄基途径均有可能，但对于3-氧代-5β-甾体而言，仅半苄基途径参与反应。通过核磁共振（NMR）和X射线衍射研究对产物进行了明确表征。
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