Diversity oriented microwave-assisted synthesis of (-)-Steganacin aza-analogues

被引:36
|
作者
Mont, Nuria [1 ]
Mehta, Vaibhav Pravinchandra [1 ]
Appukkuttan, Prasad [1 ]
Beryozkina, Tetyana
Toppet, Suzzane
Van Hecke, Kristof
Van Meervelt, Luc
Voet, Arnout
DeMaeyer, Marc
Van der Eycken, Erik [1 ]
机构
[1] Katholieke Univ Leuven, LOMAC, Dept Chem, B-3001 Louvain, Belgium
来源
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 19期
关键词
D O I
10.1021/jo801290j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel microwave-assisted, highly efficient protocol for the synthesis of hitherto unknown aza-analogues of (-)-Steganacin, a naturally occurring bisbenzocyclooctadiene lignan lactone with potent antileukemic and tubulin polymerization inhibitory activity, has been developed. Focused microwave irradiation is demonstrated to be highly beneficial in promoting the three crucial steps of the sequence to effect the final ring closure: the Suzuki-Miyaura reaction, Cu-mediated A(3)-coupling, as well as the intramolecular Huisgen 1,3-dipolar cycloaddition.
引用
收藏
页码:7509 / 7516
页数:8
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