title: A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core.
abstract: Highly functionalized and conformationally constrained depsipeptides based on a dihydropyridin-2-one core are prepared by the combination of a four- and a three-component reaction. The synthesis combines a one-pot Horner-Wadsworth-Emmons/cyclocondensation sequence leading to isonitrile-functionalized DHP-2-ones with an isonitrile-based Passerini multicomponent reaction (MCR). Substituents could be independently varied at six different positions. The two MCRs could also be performed as a one-pot procedure, simplifying the protocol and leading to a new and highly variable six-component process.
authors.affiliation: Vrije Universiteit Amsterdam, Department of Chemistry & Pharmaceutical Sciences, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.
authors.forename: Monica
authors.initials: M
authors.lastname: Paravidino
authors.forename: Rachel
authors.initials: R
authors.lastname: Scheffelaar
authors.forename: Rob F
authors.initials: RF
authors.lastname: Schmitz
authors.forename: Frans J J de
authors.initials: FJ
authors.lastname: Kanter
authors.forename: Marinus B
authors.initials: MB
authors.lastname: Groen
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
mesh_terms: D003500:Cyclization; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D047630:Depsipeptides; D011728:Pyridones