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Paper | Regular issue | Vol 32, No. 3, 1991, pp.481-488
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5654
A Convenient New Synthesis of 17-Azasteroids. Preparation of Some Novel N-Chloro-17-aza- and N-Chloro-17a-aza-17a-homosteroids as Potential Affinity Labels and Enzyme Inhibitors

Thomas G. Back,* Enoch K. Y. Lai, and Jacek W. Morzycki

*Department of Chemistry, University of Calgary, Calgary, Alberta, T2N 1N4, Canada

Abstract

An efficient new synthesis of 17-azasteroids in the estrane and androstane series was developed from readily available 16,17-seco 17-carboxylic acid precursors by means of a diphenylphosphoryl azide-mediated Curtius rearrangement as the key step. Several novel N-chloro-17-aza- and N-chloro-17a-aza-17a-homosteroids were prepared from the corresponding lactams with N-chlorosuccinimide.