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Paper | Special issue | Vol 40, No. 1, 1995, pp.205-212
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S9
Stereoselective Epoxidation of 5(10)-Ene of 11β-Functionated Steroids and Effect of 5(10)-Epoxy Group on Reaction of 11β-Substitute

Yang Suming, Yang Zhengyu, Xia Yi, and Xia Peng

*Department of Organic Chemistry, School of Pharmacy, Shanghai Medical University, 138 Yi Yuan Road Shanghai 200032, China


A route for synthesis of steroidal 5(10)α-epoxy-9(11)-ene from 11β-functionalized estr-5(10)-ene via epoxidation of 5(10)-ene and then introduction of 9(11)-ene was reported. The effect of 11β-hydroxy and acyloxy groups on stereoselective epoxidation of 5(10)-ene as well as the effect of 5(10)-epoxide configuration on some reactions of corresponding 11β-substitutes were described. A 11β-phenyl-4,9-estradiene compound has been synthesized from the 9(11)-ene-5(10)α-epoxide intermediate obtained by this route.