title: Asymmetric modular synthesis of a semirigid dipeptide mimetic by cascade cycloaddition/ring rearrangement and borohydride reduction.
abstract: A new semirigid dipeptide mimetic was prepared on multigram scale, in good yield, and in a stereocontrolled way, starting from commercially available and unexpensive reagents, i.e., N-benzylpiperidone, tosyl azide, and proline methyl ester. The optimized multicomponent process consisted of a cascade click cycloaddition and a ring rearrangement reaction, followed by a reductive step. Theoretical calculations were performed to elucidate the reaction mechanism and support the stereochemical outcome of the reduction. Finally, the new scaffold was used for the preparation of model peptidomimetics, whose β turn conformation was confirmed by dynamic NMR experiments.
authors.affiliation: Università degli Studi di Milano , DISFARM-Sez. Chimica Generale e Organica "A.Marchesini", via Venzian 21, 20133 Milano, Italy.
authors.forename: Sara
authors.initials: S
authors.lastname: Pellegrino
authors.forename: Alessandro
authors.initials: A
authors.lastname: Contini
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Gelmi
authors.forename: Leonardo
authors.initials: L
authors.lastname: Lo Presti
authors.forename: Raffaella
authors.initials: R
authors.lastname: Soave
authors.forename: Emanuela
authors.initials: E
authors.lastname: Erba
mesh_terms: D001894:Borohydrides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D004151:Dipeptides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry
chemical_list: D001894:Borohydrides; D004151:Dipeptides; D014105:Tosyl Compounds; D011392:Proline