Steroids—CXX synthesis of halogenated steroid hormones : New routes to 6α-fluorotestosterone and the 6α- and 6β- fluoro analogs of progesterone. The synthesis of 6α- and 6β-fluoro reichstein's compound “S” and 6α- and 6β- fluorodesoxycorticosterone acetate☆☆☆

摘要: Abstract The conformational and electronic factors involved in the fission of steroid 5α,6α-epoxides with boron trifluoride-etherate are discussed particular reference to C-3-keto-5α,6α-epoxides their cycloethylene-dioxy derivatives. These considerations led development a new synthesis 6-fluoro-Δ4-3-ketones from corresponding Δ4-3-ketones via cleavage derived cycloethylene-ketal-5α,6α-epoxides. Application this method 6α-fluorotestosterone 6α 6β-fluoro analogs progesterone desoxycorticosterone acetate Reichstein's Compound “S” diacetate. latter compound its Δ1-analog valuable precursors for 6-fluoro cortical hormones.