Gabbard R B, Hamer L F, Segaloff A
Steroids. 1981 Mar;37(3):243-55. doi: 10.1016/s0039-128x(81)90234-8.
The synthesis of 11 alpha-hydroxyestrone, 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxy-9 beta-estrone are presented. The reduction of 11-keto-9 beta-estrone 17-ethyleneketal by sodium in ethanol or sodium borohydride resulted in 11-hydroxy-9 beta-estrones. The 11-hydroxyl group configurations were opposite to expectations: sodium in boiling ethanol afforded the axial 11 beta-hydroxy-9 beta-estrone, while sodium borohydride in boiling tetrahydrofuran gave the equatorial 11 alpha-hydroxy-9 beta-estrone. In immature rat uterotropic bioassays using subcutaneous injections, 11 alpha-hydroxyestrone was 2 times as active as 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxyestrone was 10 times as active as 11 beta-hydroxy-9 beta-estrone.
本文介绍了11α-羟基雌酮、11α-羟基-9β-雌酮和11β-羟基-9β-雌酮的合成。在乙醇中用钠或硼氢化钠还原11-酮-9β-雌酮17-乙烯缩酮可得到11-羟基-9β-雌酮。11-羟基的构型与预期相反：在沸腾乙醇中用钠得到轴向的11β-羟基-9β-雌酮，而在沸腾四氢呋喃中用硼氢化钠得到赤道面的11α-羟基-9β-雌酮。在使用皮下注射的未成熟大鼠子宫增重生物测定中，11α-羟基雌酮的活性是11α-羟基-9β-雌酮的2倍，11β-羟基雌酮的活性是11β-羟基-9β-雌酮的10倍。
