Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic

Byoung J. Min, Xuyuan Gu, Takashi Yamamoto, Ravil R. Petrov, Hongchang Qu, Yeon Sun Lee, Victor J. Hruby

Research output: Contribution to journalArticle

12 Scopus citations

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 Nα-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.

Original languageEnglish (US)
Pages (from-to)2316-2319
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number14
DOIs
StatePublished - Mar 31 2008

Keywords

  • Acetals
  • Internal bicyclic peptidomimetics
  • N-Acylimnium ion cyclization

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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