Synthesis of Oxygen-Bridged Antigestagens

Article abstract of DOI:10.1016/S0040-4020(01)80365-3

A synthetic access to 10,11β-(oxy-1,2-phenylene)-steroids 13 is described.Key steps are the S_N2' type introduction of suitably ortho substituted arenes into vinyl epoxide 4, and ring closure by an acid catalysed intramolecular epoxide opening with the corresponding phenol.The resulting oxygen bridged steroids 13 are transformed into pharmacologically relevant progesterone antagonists 19a-c and 20.Key Words: antigestagens; 11β-substituted steroids; 10,11β-(oxy-1,2-phenylene)-steroids; acid catalysed intramolecular epoxide opening