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 Citations (Scopus)

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

Fingerprint

Peptidomimetics
Acetals
Cyclization
Amides
Conformations
Nitrogen
Ions
Derivatives

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic. / Min, Byoung J.; Gu, Xuyuan; Yamamoto, Takashi; Petrov, Ravil R.; Qu, Hongchang; Lee, Yeon Sun; Hruby, Victor J.

In: Tetrahedron Letters, Vol. 49, No. 14, 31.03.2008, p. 2316-2319.

Research output: Contribution to journalArticle

Min, Byoung J. ; Gu, Xuyuan ; Yamamoto, Takashi ; Petrov, Ravil R. ; Qu, Hongchang ; Lee, Yeon Sun ; Hruby, Victor J. / Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 14. pp. 2316-2319.
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