Total Synthesis of a Marine Alkaloid-Rigidin E

被引：16

作者：

Cao, Banpeng ^{[1
]}

Ding, Haixin ^{[1
]}

Yang, Ruchun ^{[1
]}

Wang, Xiaoji ^{[1
]}

Xiao, Qiang ^{[1
]}

机构：

[1] Jiangxi Sci & Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Peoples R China

来源：

MARINE DRUGS | 2012年 / 10卷 / 06期

关键词：

pyrrolo[2,3-d]pyrimidine; alkaloids; total synthesis; domino reaction; marine natural products; DERIVATIVES; ANALOGS; NUCLEOSIDE; EFFICIENT;

D O I：

10.3390/md10061412

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

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 I-2 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.

引用

页码：1412 / 1421

页数：10

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