Passerini reaction-amine deprotection-acyl migration peptide assembly: efficient formal synthesis of cyclotheonamide C.
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.
Faure
Sophie
S
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
Hjelmgaard
Thomas
T
Roche
Stéphane P
SP
Aitken
David J
DJ
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D010455:Peptides; D010456:Peptides, Cyclic; C096691:cyclotheonamide C