Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic.
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.
Min
Byoung J
BJ
Department of Chemistry, University of Arizona, Tucson, AZ 85721, USA.
Gu
Xuyuan
X
Yamamoto
Takashi
T
Petrov
Ravil R
RR
Qu
Hongchang
H
Lee
Yeon Sun
YS
Hruby
Victor J
VJ