Synthesis and biological activity of two new D-secoestrone derivatives

摘要

Addition of phenyl lithium to 3-methoxyestra-1, 3,5 (10)-trien-16, 17-dione 16- oxime (1) afforded the corresponding 17α-phenyl-17β-hydroxy derivative 2, which, under Beckmann fragmentation reaction conditions, gave the 16, 17-seco derivative 3. Sodium borohydride reduction of the primary fragmentation product resulted in form- Tion of a sole product 4, which, according to X-ray structural analysis, represents the 17(S)-isomer. In biological tests both compounds 3 and 4 showed practically a complete loss of estrogenic activity.