The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E
The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E
复制标题
DOI：
10.1016/j.tet.2006.06.047
复制
发表时间：
2006-08-28
期刊：
影响因子：
2.1
通讯作者：
Sikorski, James A.
中科院分区：
文献类型：
--
作者：
Gupton, John T.;Banner, Edith J.;Sikorski, James A.
本文叙述了利用葡萄酸盐合成含海洋天然产物刚性蛋白和刚性蛋白E的吡咯的研究。成功的策略依赖于由vinamidinium盐形成2,4-二取代吡咯，然后在吡咯的5位进行酰化。吡咯3位卤化和氨基羰基化，C-2位酯基水解，Curtius重排生成吡咯嘧啶骨架。最后的去保护步骤完成了Rigidin和Rigidin e的合成(c) 2006 Elsevier Ltd.。版权所有。
Studies directed on the synthesis of the pyrrole containing marine natural products Rigidin and Rigidin E via vinylogous iminium salts are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole from a vinamidinium salt followed by acylation at the 5-position of pyrrole. Halogenation and aminocarbonylation at the 3-position of pyrrole followed by hydrolysis of the ester group at C-2 and subsequent Curtius rearrangement generates the pyrrolopyrimidine skeleton. A final deprotection step completes the synthesis of Rigidin and Rigidin E. (c) 2006 Elsevier Ltd. All rights reserved.