用三氟甲磺酸酐（Tf2O）和吡啶对内酰胺进行亲电活化：（±）-四ponerine T4的简便合成

Electrophilic activation of lactams with Tf2O and pyridine: expedient synthesis of (+/-)-tetraponerine T4.

作者信息

Charette André B, Mathieu Simon, Martel Jonathan

机构信息

Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada, H3C 3J7.

出版信息

Org Lett. 2005 Nov 24;7(24):5401-4. doi: 10.1021/ol052069n.

DOI:10.1021/ol052069n

PMID:16288516

Abstract

[reaction: see text] The electrophilic activation of lactams with triflic anhydride in the presence of pyridine was investigated by NMR. It was found that 2-pyrrolidone led to the clean formation of the corresponding pyridinium imidate in 89% isolated yield. The subsequent nucleophilic addition of organometallic reagents led to 2-substituted dihydropyridines. A synthesis of (+/-)-tetraponerine T4 with three simple building blocks was accomplished in 3 steps (38% yield).

摘要

[反应：见正文] 通过核磁共振研究了在吡啶存在下用三氟甲磺酸酐对内酰胺进行亲电活化。发现2-吡咯烷酮能以89%的分离产率顺利形成相应的吡啶基亚氨酸酯。随后有机金属试剂的亲核加成生成了2-取代的二氢吡啶。通过三步反应（产率38%）完成了用三个简单结构单元合成（±）-四环肽T4。