title: Optimization of the abnormal Beckmann rearrangement: application to steroid 17-oximes.
abstract: 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.
authors.affiliation: Department of Chemistry, Nanjing University, P R China.
authors.forename: Cunde
authors.initials: C
authors.lastname: Wang
authors.forename: Xin
authors.initials: X
authors.lastname: Jiang
authors.forename: Haijian
authors.initials: H
authors.lastname: Shi
authors.forename: Jun
authors.initials: J
authors.lastname: Lu
authors.forename: Yuefei
authors.initials: Y
authors.lastname: Hu
authors.forename: Hongwen
authors.initials: H
authors.lastname: Hu