Efficient synthesis of the structural core of tetracyclines by a palladium-catalyzed domino Tsuji-Trost-Heck-Mizoroki reaction

被引：14
|
作者：
Tietze, Lutz F. [1 ]
Redert, Thomas [1 ]
Bell, Hubertus P. [1 ]
Hellkamp, Sascha [1 ]
Levy, Laura M. [1 ]
机构：
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 08期
关键词：
antibiotics domino reactions; metathesis; palladium; tetracyclines;
D O I：
10.1002/chem.200701676
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Pd-catalyzed domino Tsuji-Trost-Heck-Mizoroki reactions of compounds 18, 27, and 34, respectively, each containing an allyl acetate and a halogen aryl moiety, lead to the formation of hexahydronaphthacenes 2 and 3 and octahydroanthracene 4 in 62-81% yield. The octahydroanthracene and hexahydronaphthacene motifs are found in many natural products, for example, the tetracycline antibiotics.
引用
收藏
页码：2527 / 2535
页数：9
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