Total Synthesis of a Marine Alkaloid—Rigidin E

Marine Drugs

Banpeng Cao²  Haixin Ding²  Ruchun Yang²  Xiaoji Wang¹ 

[1] Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, China;

关键词: pyrrolo[2;    3-d]pyrimidine;    alkaloids;    total synthesis;    domino reaction;    marine natural products;   

DOI  :  10.3390/md10061412

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.