Regioselective synthesis of spiropyrrolidine/spiropyrrolizidine/spirothiazolidine-grafted macrocycles through 1,3-dipolar cycloaddition methodology
作者:S. Purushothaman、R. Prasanna、R. Raghunathan
DOI:10.1016/j.tet.2013.09.015
日期:2013.11
Synthesis of 13- and 16-membered macrocyclic enone with alkyl ether and triazole as a linker was achieved using intramolecular aldol condensation. The newly synthesized macrocyclic enone was successfully utilized as a dipolarophile in 1,3-dipolar cycloaddition (1,3-DC). The dipole generated from isatin/acenaphthenequinone with various secondary amino acids (sarcosine, l-proline, and thiazolidine-4-carboxylic
的13-和合成16-元大环烯酮与烷基醚和三唑作为接头,使用分子内羟醛缩合来实现的。新合成的大环烯酮被成功地用作1,3-偶极环加成(1,3-DC)亲偶极。(肌氨酸,与各种仲氨基酸从靛红/苊醌产生的偶极升噻唑烷-4-羧酸-脯氨酸,和)与大环烯酮反应,得到一类新的以良好的收率spiropyrrolidine接枝大环化合物(> 85%)的。结构通过2D NMR谱分配和cycloadducts的区域选择性和立体化学结果通过单晶X-射线分析确定。