Three-Component One-Pot Total Syntheses of Glyantrypine, Fumiquinazoline F, and Fiscalin B Promoted by Microwave Irradiation

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 se...

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Veröffentlicht in:Journal of organic chemistry 2005-08, Vol.70 (16), p.6339-6345
Hauptverfasser: Liu, Ji-Feng, Ye, Ping, Zhang, Bailin, Bi, Grace, Sargent, Katie, Yu, Libing, Yohannes, Daniel, Baldino, Carmen M
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0508043