Total Synthesis of Sequential Retro??Peptide Oligomers

…, F Formaggio, M Crisma, C Toniolo…

Index: Ceretti, Simone; Luppi, Gianluigi; De Pol, Silvia; Formaggio, Fernando; Crisma, Marco; Toniolo, Claudio; Tomasini, Claudia European Journal of Organic Chemistry, 2004 , # 20 p. 4188 - 4196

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Citation Number: 8

Abstract

Abstract The total synthesis of sequential oligomers of retro-peptides of the general formula Boc (-gGly-mAib) n-OBn, starting from dimethylmalonic acid, has been carried out in good overall yield. The key step is the formation of the gGly unit> N− CH 2− N<, which is easily obtained in a one-pot/three-step reaction from BnO-mAib-Gly-OH and diphenylphosphoryl azide. The synthesis of the sequential oligomers of RCO (-gAla-mAib) n-OR′ was also ...