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

M. Paravidino, R. Scheffelaar, R.F. Schmitz, F.J.J. de Kanter, M.B. Groen, E. Ruijter, R.V.A. Orru

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

(Chemical Equation Presented) 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. © 2007 American Chemical Society.
Original languageEnglish
Pages (from-to)10239-42
JournalJournal of Organic Chemistry
Volume72
Issue number26
DOIs
Publication statusPublished - 2007

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