一种新型苄基八氢吡嗪并[1,2 - a]嘧啶 - 6 - 酮衍生物的合成，作为一种便捷的内部双环肽模拟物。
Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic.
作者信息
Min Byoung J, Gu Xuyuan, Yamamoto Takashi, Petrov Ravil R, Qu Hongchang, Lee Yeon Sun, Hruby Victor J
机构信息
Department of Chemistry, University of Arizona, Tucson, AZ 85721, USA.
出版信息
Tetrahedron Lett. 2008 Mar 31;49(14):2316-2319. doi: 10.1016/j.tetlet.2008.01.137.
Abstract
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(α)-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.
摘要
通过酰胺氮与由Cbz保护的氨基丙基 - 苯丙氨酰胺衍生的N(α)-缩醛之间的分子内N-酰基亚胺离子环化反应，立体选择性地合成了一种取代的氢吡嗪并[1,2-a]嘧啶-6-酮衍生物，产率很高。单一非对映异构体的形成归因于其双环结构的低能量椅式构象。该方法为构建内部双环肽模拟物提供了一种便捷工具。
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