A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core

Monica Paravidino; Rachel Scheffelaar; Rob F Schmitz; Frans J J de Kanter; Marinus B Groen; Eelco Ruijter; Romano V A Orru

doi:10.1021/jo701978v

A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core

J Org Chem. 2007 Dec 21;72(26):10239-42. doi: 10.1021/jo701978v. Epub 2007 Nov 13.

Authors

Monica Paravidino¹, Rachel Scheffelaar, Rob F Schmitz, Frans J J de Kanter, Marinus B Groen, Eelco Ruijter, Romano V A Orru

Affiliation

¹ Vrije Universiteit Amsterdam, Department of Chemistry & Pharmaceutical Sciences, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.

PMID: 17997575
DOI: 10.1021/jo701978v

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Depsipeptides / chemical synthesis*
Depsipeptides / chemistry*
Molecular Structure
Pyridones / chemistry*
Stereoisomerism

Substances

Depsipeptides
Pyridones