Three-Component One-Pot Total Syntheses of Glyantrypine, Fumiquinazoline F, and Fiscalin B Promoted by Microwave Irradiation
The Journal of Organic Chemistry2005Vol. 70(16), pp. 6339–6345
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Jifeng Liu, Ye Ping, Bailin Zhang, Grace Bi, Katie Sargent, Libing Yu, Daniel Yohannes, Carmen M. Baldino
Abstract
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.
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