Synthesis of Lactam-Based Peptidomimetics from β-Keto Esters and β-Keto Amides

Article abstract of DOI:10.1021/jo991306v

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.