Steroids

Synthesis of 4-and 16α-hydroxylated equine estrogens

I Shigeo, K Takao, T Masahiko

Index: Ikegawa, Shigeo; Kurosawa, Takao; Tohma, Masahiko Steroids, 1990 , vol. 55, # 6 p. 250 - 255

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Citation Number: 4

Abstract

Abstract 4-Hydroxyequilin, 4-hydroxyequilenin, and 16α-hydroxyequilenin were synthesized as authentic specimens for the metabolic studies of equine estrogens. The synthetic route leading to the 4-hydroxylated compounds was started from o-vanillin, which was transformed into the β-ketosulfoxide (2b) by sequential multistep reactions. This was converted to the α, β-unsaturated ketone (3) as Michael acceptor. Condensation of 3 with ...