jo050736k_si_002.pdf (8.41 MB)
0/0

Synthesis of 4-Substituted-3-aminopiperidin-2-ones:  Application to the Synthesis of a Conformationally Constrained Tetrapeptide N-Acetyl-Ser-Asp-Lys-Pro

Download (8.41 MB)
journal contribution
posted on 22.07.2005 by Sukeerthi Kumar, Céline Flamant-Robin, Qian Wang, Angèle Chiaroni, N. André Sasaki
A new and practical synthetic strategy is developed for the synthesis of six-membered lactam-bridged dipeptides, 4-substituted-3-aminopiperidin-2-ones, featuring two key steps:  (a) a diastereoselective addition of cuprate to (E)-α,β-unsaturated ester (3) and (b) racemization-free reductive amination. On the basis of this methodology, conformationally constrained tetrapeptide N-acetyl-Ser-Asp-Lys-Pro (AcSDKP) (2) has been successfully synthesized from 3-amino-4-vinylpiperidin-2-one (22).

History

Exports