Diversity-oriented synthesis of tamoxifen-type tetrasubstituted olefins
Diversity-oriented synthesis of tamoxifen-type tetrasubstituted olefins
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DOI：
10.1021/ja037566i
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发表时间：
2003-12-03
影响因子：
15
通讯作者：
Yoshida, J
中科院分区：
文献类型：
--
作者：
Itami, K;Kamei, T;Yoshida, J
基于新型铜催化的炔基（2-吡啶基）硅烷的碳镁化反应，发展了一种合成他莫昔芬型四取代烯烃的通用方案。可以以区域控制、立体控制和多样性取向的方式制备各种各样的电子和结构不同的四取代烯烃。值得注意的特征是（i）三个芳基被认为对于抗雌激素活性是重要的（必需的），可以随意变化，因为它们都来自容易获得的芳基碘，和（ii）任何立体异构体和区域异构体原则上可以通过简单地改变芳基碘的应用顺序来制备。
A general synthetic scheme for tamoxifen-type tetrasubstituted olefins based on the novel Cu-catalyzed carbomagnesation across alkynyl(2-pyridyl)silane has been developed. A wide array of electronically and structurally diverse tetrasubstituted olefins can be prepared in a regiocontrolled, stereocontrolled, and diversity-oriented manner. Noteworthy features are that (i) the three aryl groups, which are believed to be important (essential) for anti-estrogenic activity, can be varied at will because they all stem from readily available aryl iodides, and (ii) any stereo- and regioisomers can, in principle, be prepared by simply changing the applying order of aryl iodides into the sequence.