SYNTHETIC APPROACH TO ANALOGUES OF 19 NORSTEROIDS WITH AN ACYCLIC SIDE CHAIN
SYNTHETIC APPROACH TO ANALOGUES OF 19 NORSTEROIDS WITH AN ACYCLIC SIDE CHAIN
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DOI：
10.1016/0039-128x(89)90149-9
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发表时间：
1989-01-01
期刊：
影响因子：
2.7
通讯作者：
TURECEK F
中科院分区：
文献类型：
--
作者：
DRASAR P;POUZAR V;TURECEK F
外消旋14. beta. -羟基- 3 -甲氧基- 8. -α,α。9.通过全合成得到- 1,3,5(10)-雌二醇-17- 1 (I)，转化为具有烷氧羰基乙烯侧链的衍生物rac-(2OE)-21-甲氧羰基-19-no -8.,9. α。-孕- 1,3,5(10)，20-四烯-3,14 β。-二醇3-甲基醚（XII），采用两次Wittig反应。5的类似导数。制备-雄甾烷作为合成模型。研究了甾烷系列中17位侧链的立体化学、部分化合物的生物活性及其色谱性质。
Racemic 14.beta.-hydroxy-3-methoxy-8.alpha.,9.alpha.-1, 3, 5 (10)-estratriene-17-one (I), obtained by total synthesis, was converted into a derivative with alkoxycarbonylethylenic side chain, rac-(2OE)-21-methoxycarbonyl-19-nor-8.alpha.,9.alpha.-pregna-1, 3, 5(10), 20-tetraene-3,14.beta.-diol 3-methyl ether (XII) using two Wittig reactions. Analogous derivatives of 5.alpha.-androstane were prepared as synthetic models. In the estrane series the stereochemistry of attachment of the side chain in position 17, biological activity of some compounds, and their chromatographic properties were investigated.