title: Passerini reaction-amine deprotection-acyl migration peptide assembly: efficient formal synthesis of cyclotheonamide C.
abstract: A short, convergent, formal total synthesis of cyclotheonamide C is described. The key linear pentapeptide intermediate is assembled at the same time as the elaboration of the alpha-hydroxyhomoarginine (H-hArg) residue via a three-component Passerini reaction-amine deprotection-O,N-acyl migration strategy.
authors.affiliation: Laboratoire de Synthèse et Etude de Systèmes d'Intérêt Biologique, SEESIB (UMR 6504-CNRS), Université Blaise Pascal-Clermont-Ferrand 2, 24 avenue des Landais, 63177 Aubière Cedex, France. sophie.faure@univ-bpclermont.fr
authors.forename: Sophie
authors.initials: S
authors.lastname: Faure
authors.forename: Thomas
authors.initials: T
authors.lastname: Hjelmgaard
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Roche
authors.forename: David J
authors.initials: DJ
authors.lastname: Aitken
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D010455:Peptides; D010456:Peptides, Cyclic; C096691:cyclotheonamide C