Diversity-oriented synthesis of tamoxifen-type tetrasubstituted olefins.
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.
Itami
Kenichiro
K
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
Kamei
Toshiyuki
T
Yoshida
Jun-ichi
J
D000475:Alkenes / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry; D013629:Tamoxifen / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000475:Alkenes; D012821:Silanes; D013629:Tamoxifen