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A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
16
Identifiers
DOI: 10.1016/j.tetlet.2004.02.117
Keywords
  • Bicyclic Dipeptide
  • β-Substituted Aspartic Acid
  • Trifluoroacetamide
  • Cholecystokinin

Abstract

Abstract Alkylation of N α-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral β-allyl substituted aspartic acid in good yields. After deprotection of the N α-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with l-cysteine through a cascade three-bond formation process to afford aspartic acid–glycine bicyclic dipeptide mimetics.

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