Constrained analogs of methionine: Asymmetric synthesis of χ-angle restricted methionine derivatives through [3.1.0]-γ-lactone cyclopropane ring opening

Chang Sun Lee, Kee In Lee, Andrew Hamilton

Research output: Contribution to journalArticle

Abstract

Regiospecific and stereoselective ring opening of a [3.1.0]-γ-lactone intermediate by sulfur-containing nucleophiles has been developed. The reaction product was confirmed by NMR techniques and chemical equilibrium processes. Using this approach, all four possible diastereomers of χ-angle restricted methionine surrogates have been synthesized by electrophilic azidation and reduction to the amino group. These constrained analogs can be used in the preparation of peptidomimetics of sequences containing methionine in the C-terminal position.

Original languageEnglish (US)
Pages (from-to)211-213
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number2
DOIs
StatePublished - Jan 8 2001

Fingerprint

Lactones
Methionine
Chemical Phenomena
Peptidomimetics
Derivatives
Nucleophiles
Reaction products
Sulfur
Nuclear magnetic resonance
cyclopropane

Keywords

  • [3.1.0]-γ-lactone
  • Constrained methionine analogs
  • Peptidomimetics

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Constrained analogs of methionine : Asymmetric synthesis of χ-angle restricted methionine derivatives through [3.1.0]-γ-lactone cyclopropane ring opening. / Lee, Chang Sun; Lee, Kee In; Hamilton, Andrew.

In: Tetrahedron Letters, Vol. 42, No. 2, 08.01.2001, p. 211-213.

Research output: Contribution to journalArticle

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