A novel, highly selective, and general methodology for the synthesis of 1,5-diene-containing oligoisoprenoids of all possible geometrical combinations exemplified by an iterative and convergent synthesis of coenzyme Q(10).

A novel, highly selective, and general methodology for the synthesis of 1,5-diene-containing oligoisoprenoids of all possible geometrical combinations exemplified by an iterative and convergent synthesis of coenzyme Q(10).
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DOI:
10.1021/ol010263d
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发表时间:
2002-01
期刊:
影响因子:
5.2
通讯作者:
E. Negishi;Show-Yee Liou;Caiding Xu;Shouquan Huo
E. Negishi;Show-Yee Liou;Caiding Xu;Shouquan Huo
中科院分区:
化学1区
文献类型:
--
作者:
E. Negishi;Show-Yee Liou;Caiding Xu;Shouquan Huo

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[reaction: see text] A truly general, versatile, and highly regio- and stereoselective methodology for the synthesis of terpenoids containing 1,5-diene units of E and/or Z geometry critically involves Pd-catalyzed homoallyl- and homopropargyl-alkenyl coupling and Zr-catalyzed carboalumination of alkynes. By using this methodology, coenzyme Q(10), (E,Z,E)-geranylgeranoil, and other natural or unnatural compounds have been synthesized efficiently.