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

doi:10.1021/jo701978v

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

Organic Chemistry

Research output: Contribution to Journal › Article › Academic › peer-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 language	English
Pages (from-to)	10239-42
Journal	Journal of Organic Chemistry
Volume	72
Issue number	26
DOIs	https://doi.org/10.1021/jo701978v
Publication status	Published - 2007

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title = "A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridinone core",

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. {\textcopyright} 2007 American Chemical Society.",

author = "M. Paravidino and R. Scheffelaar and R.F. Schmitz and {de Kanter}, F.J.J. and M.B. Groen and E. Ruijter and R.V.A. Orru",

year = "2007",

doi = "10.1021/jo701978v",

language = "English",

volume = "72",

pages = "10239--42",

journal = "Journal of Organic Chemistry",

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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

Y1 - 2007

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.

U2 - 10.1021/jo701978v

DO - 10.1021/jo701978v

M3 - Article

SN - 0022-3263

VL - 72

SP - 10239

EP - 10242

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

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

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