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

Total Synthesis of a Marine Alkaloid—Rigidin E

*  and *
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 / Revised: 7 June 2012 / Accepted: 8 June 2012 / Published: 20 June 2012
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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 (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Cao, B.; Ding, H.; Yang, R.; Wang, X.; Xiao, Q. Total Synthesis of a Marine Alkaloid—Rigidin E. Mar. Drugs 2012, 10, 1412-1421.

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