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Total Synthesis of a Marine Alkaloid—Rigidin E
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, China
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Received: 28 May 2012; in revised form: 7 June 2012 / Accepted: 8 June 2012 / Published: 20 June 2012
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-(benzyloxy)phenyl)-2-oxoethyl)methanesulfonamide and 3-(4-(benzyloxy)phenyl)-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.
Keywords: pyrrolo[2,3-d]pyrimidine; alkaloids; total synthesis; domino reaction; marine natural products
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MDPI and ACS Style
Cao, B.; Ding, H.; Yang, R.; Wang, X.; Xiao, Q. Total Synthesis of a Marine Alkaloid—Rigidin E. Mar. Drugs 2012, 10, 1412-1421.
Cao B, Ding H, Yang R, Wang X, Xiao Q. Total Synthesis of a Marine Alkaloid—Rigidin E. Marine Drugs. 2012; 10(6):1412-1421.
Cao, Banpeng; Ding, Haixin; Yang, Ruchun; Wang, Xiaoji; Xiao, Qiang. 2012. "Total Synthesis of a Marine Alkaloid—Rigidin E." Mar. Drugs 10, no. 6: 1412-1421.