Total Synthesis of a Marine Alkaloid—Rigidin E

doi:10.3390/md10061412

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

Communication

Total Synthesis of a Marine Alkaloid—Rigidin E

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

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

* Authors to whom correspondence should be addressed.

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

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Cite This Article

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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