Synthesis of Lactam-Based Peptidomimetics from β-Keto Esters and β-Keto Amides
The Journal of Organic Chemistry1999Vol. 64(26), pp. 9668–9672
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Abstract
Pyrrolidinone-based peptidomimetics, in which the peptide bond is forced to adopt either a cis or trans geometry, have been prepared from readily available amino acids. Peptidomimetics based on amino acid side chain to side chain cyclization (17), side chain to N cyclization (18), and α-H to side chain cyclization (28) have been developed. A key step in the syntheses is the treatment of a peptide-based β-keto ester or amide with an amine. The absolute configuration of compounds 28 was established using Seebach oxazolidinone chemistry.
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