Analog 3a, which contains Val instead of the Aib-3 residue of Balaram's peptide, was synthesized as shown in Scheme 4. The dipeptide Cbz-Aib-Pro was coupled with racemic -OH-Val derivative 14 to afford tripeptide 15 in good yield. Saponification of this peptide was followed by dehydration and azlactone formation utilizing NaOAc and Ac2O in THF. Ring-opening and coupling of the hindered azlactone intermediate was difficult. A brief survey of conditions revealed that serviceable yields of tetrapeptide 3a could be obtained by first hydrolyzing the azlactone through treatment with NaOH and then employing PyBOP to mediate coupling with Ala-OMe.