期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 68, 期 11, 页码 4579-4581出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo034142y
关键词
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A novel and practical procedure was developed for the abnormal Beckmann rearrangement of steroid 17-oximes. Treatment of the 17-oximes with TFA/CH(OMe)(3) in boiling THF for 2 h gives the corresponding 13,17-seco alkene nitrile products in unprecedented high yields (70-92%). Since the alkene nitriles can be subsequently converted into 18-norsteroids, this general method provides a highly efficient route to these biologically important compounds and, by extension, to other structurally related natural products.
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