Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic
- 作者：Byoung J. Min ; Xuyuan Gu ; Takashi Yamamoto ; Ravil R. Petrov ; Hongchang Qu ; Yeon Sun Lee ; Victor J. Hruby
- 关键词：Internal bicyclic peptidomimetics ; N-Acylimnium ion cyclization ; Acetals
- 刊名：Tetrahedron Letters
- 出版年：2008
- 期刊代码：109_00404039
- 类别：ch
- 出版时间：31 March 2008
- 卷：49
- 期：14
- 页码：2316-2319
- 文件大小：231 K
摘要
A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an N
-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics.
-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics.