Wang Cunde, Rath Nigam P, Covey Douglas F
Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 South Euclid Avenue, St. Louis, MO, 63110, USA.
Tetrahedron Lett. 2006 Nov 6;47(45):7837-7839. doi: 10.1016/j.tetlet.2006.09.027.
The synthesis of Delta(13,(17))-androgens and the structurally related 13,17-epoxides is described. The synthetic route involves cleavage of 17-ketosteroids by an abnormal Beckmann rearrangement, modification of the D-ring cleavage product to obtained an intermediate tricyclic diene and ring closing metathesis of the diene to the Delta(13,(17))-androgen. (3alpha,5alpha)-Androst-13(17)-en-3-ol and the derivative 13alpha,17alpha- and 13beta,17beta- epoxides were prepared by this route.
描述了Δ(13,(17))-雄激素及其结构相关的13,17-环氧化物的合成。合成路线包括通过异常贝克曼重排裂解17-酮甾体，将D环裂解产物进行修饰以得到中间体三环二烯，以及将该二烯进行闭环复分解反应生成Δ(13,(17))-雄激素。通过该路线制备了(3α,5α)-雄甾-13(17)-烯-3-醇及其13α,17α-和13β,17β-环氧化物衍生物。
