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Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, China





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Abstract In the present paper, we report an efficient total synthesis of a marine alkaloid, rigidin E. The key tetrasubstituted 2-amino-3-carboxamidepyrrole intermediate was synthesized by cascade Michael addition-intramolecular cyclization between N-2-4-benzyloxyphenyl-2-oxoethylmethanesulfonamide and 3-4-benzyloxyphenyl-2-cyano-N-methylacrylamide. Subsequent carbonylation with triphosgene catalyzed by I2 and deprotection of benzyl groups afforded rigidin E in 21% overall yield. This strategy has the merits of metal-free reactions, low cost, mild reaction protocols, and easy access to diversity-oriented derivatives for potential structure-activity relationship investigation. View Full-Text

Keywords: pyrrolo2,3-dpyrimidine; alkaloids; total synthesis; domino reaction; marine natural products pyrrolo2,3-dpyrimidine; alkaloids; total synthesis; domino reaction; marine natural products





Autor: Banpeng Cao, Haixin Ding, Ruchun Yang, Xiaoji Wang * and Qiang Xiao *

Fuente: http://mdpi.com/



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