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