Three-component one-pot total syntheses of glyantrypine, fumiquinazoline F, and fiscalin B promoted by microwave irradiation

被引:95
作者
Liu, JF [1 ]
Ye, P [1 ]
Zhang, BL [1 ]
Bi, G [1 ]
Sargent, K [1 ]
Yu, LB [1 ]
Yohannes, D [1 ]
Baldino, CM [1 ]
机构
[1] ArQule Inc, Div Chem Technol, Woburn, MA 01801 USA
关键词
D O I
10.1021/jo0508043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. By adapting this synthetic strategy through the use of selected Boc-amino acids and amino acid esters, we have accomplished highly efficient and concise total syntheses of glyantrypine (2), fumiquinazoline F (3), and fiscalin B (5), achieving overall yields of 55, 39, and 20%, respectively.
引用
收藏
页码:6339 / 6345
页数:7
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