A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core.
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.
Paravidino
Monica
M
Vrije Universiteit Amsterdam, Department of Chemistry & Pharmaceutical Sciences, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.
Scheffelaar
Rachel
R
Schmitz
Rob F
RF
Kanter
Frans J J de
FJ
Groen
Marinus B
MB
Ruijter
Eelco
E
Orru
Romano V A
RV
D003500:Cyclization; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
D047630:Depsipeptides; D011728:Pyridones