17 alpha -Alkanoyloxy-11 beta -methyl-19-norpregn-4-ene-3,20-diones are converted to the corresponding enol ethers by standard methods and the latter derivatives are, alternatively, oxidized to yield the corresponding 4,6-diene-3,20-diones or are contacted first with an N-chloroamide or N-chloroimide, e.g., N-chlorosuccinimide, then with a strong mineral acid to yield the 6 alpha -chloro compounds. Reaction of the aforementioned 4,6-diene-3,20-diones with a peracid results in the corresponding 6 alpha ,7 alpha -epoxy-3-keto- DELTA 4 compounds, which are contacted with a hydrogen halide, and the resulting 6 beta -chloro-7 alpha -hydroxy compounds are dehydrated by conversion first to the 7-methanesulfonate followed by heating with a suitable base to provide the desired 6-chloro-3-keto- DELTA 4,6 derivatives. The compounds of this invention are unusually potent progestational and estrogen-inhibitory agents.
展开▼
