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

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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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Paravidino, M. ; Scheffelaar, R. ; Schmitz, R.F. ; de Kanter, F.J.J. ; Groen, M.B. ; Ruijter, E. ; Orru, R.V.A. / A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 26. pp. 10239-42.
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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. {\circledC} 2007 American Chemical Society.",
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A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core. / Paravidino, M.; Scheffelaar, R.; Schmitz, R.F.; de Kanter, F.J.J.; Groen, M.B.; Ruijter, E.; Orru, R.V.A.

In: Journal of Organic Chemistry, Vol. 72, No. 26, 2007, p. 10239-42.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core

AU - Paravidino, M.

AU - Scheffelaar, R.

AU - Schmitz, R.F.

AU - de Kanter, F.J.J.

AU - Groen, M.B.

AU - Ruijter, E.

AU - Orru, R.V.A.

PY - 2007

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N2 - (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.

AB - (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.

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EP - 10242

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

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ER -