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

✍ Scribed by Chang-Sun Lee; Kee-In Lee; Andrew D Hamilton

Book ID: 104211456
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 69 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01912-2

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✦ Synopsis

Regiospecific and stereoselective ring opening of a [3.1.0]-g-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 x-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.

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ChemInform Abstract: Constrained Analogues of Methionine: Asymmetric Synthesis of χ-Angle Restricted Methionine Derivatives Through [3.1.0]-γ-Lactone Cyclopropane Ring Opening.

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