Synthesis of β-phenyl-δ,ε-unsaturated amino acids and stereoselective introduction of side chain groups into [4,3,0]-bicyclic β-turn dipeptides

Xuyuan Gu, Scott Cowell, Jinfa Ying, Xuejun Tang, Victor J. Hruby

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

(2S,3S)- and (2R,3R)-2-amino-3-phenyl-5-hexenoic acids have been synthesized in large scale by using Ni(II)-complexes as a template. The amino acids were used in the synthesis of [4,3,0]-bicyclic β-turn mimetics by a convergent methodology. The unique advantage of this strategy is the convenience of introducing side chain groups with predetermined chiralities on both the five- and six-membered heterocyclic rings.

Original languageEnglish (US)
Pages (from-to)5863-5866
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number31
DOIs
StatePublished - Jul 28 2003

    Fingerprint

Keywords

  • Bicyclic dipeptide
  • Ni(II)-complex
  • β-side chain
  • β-turn mimetic
  • δ,ε-unsaturated amino acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this