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Mar. Drugs 2012, 10(6), 1412-1421; doi:10.3390/md10061412
Communication

Total Synthesis of a Marine Alkaloid—Rigidin E

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Received: 28 May 2012; in revised form: 7 June 2012 / Accepted: 8 June 2012 / Published: 20 June 2012
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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-(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 pyrrolo[2,3-d]pyrimidine; alkaloids; total synthesis; domino reaction; marine natural products
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

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.

Chicago/Turabian Style

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.


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