Undecylenic acid: A valuable renewable building block on route to Tyromycin A derivatives

Steen, Michael; Stevens, Christian V.; Eeckhout, Yves; Buyck, L. De; Ghelfi, Franco; Roncaglia, Fabrizio

doi:10.1002/ejlt.200800024

Cited by 22 publications

(8 citation statements)

References 27 publications

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“…However, the homoallylic hydroxyl group may also prevent alkene metathesis [76][77][78][79]. We thus studied the cross-metathesis of methyl ricinoleate 22 with acrylonitrile using both the single dose addition and the dropwise slow addition of catalyst IV (Scheme 11).…”

Section: Cross-metathesis Of Methyl Ricinoleate With Acrylonitrile Anmentioning

confidence: 99%

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Alkene Metathesis Catalysis: A Key for Transformations of Unsaturated Plant Oils and Renewable Derivatives

Dixneuf

Bruneau

Fischmeister

2016

Oil Gas Sci. Technol. – Rev. IFP Energies nouvelles

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-This account presents the importance of ruthenium-catalysed alkene cross-metathesis for the catalytic transformations of biomass derivatives into useful intermediates, especially those developed by the authors in the Rennes (France) catalysis team in cooperation with chemical industry. The cross-metathesis of a variety of functional alkenes arising from plant oils, with acrylonitrile and fumaronitrile and followed by catalytic tandem hydrogenation, will be shown to afford linear amino acid derivatives, the precursors of polyamides. The exploration of crossmetathesis of bio-sourced unsaturated nitriles with acrylate with further catalytic hydrogenation has led to offer an excellent route to a,x-amino acid derivatives. That of fatty aldehydes has led to bifunctional long chain aldehydes and saturated diols. Two ways of access to functional dienes by ruthenium-catalyzed ene-yne cross-metathesis of plant oil alkene derivatives with alkynes and by cross-metathesis of bio-sourced alkenes with allylic chloride followed by catalytic dehydrohalogenation, are reported. Ricinoleate derivatives offer a direct access to chiral dihydropyrans and tetrahydropyrans via ring closing metathesis. Cross-metathesis giving value to terpenes and eugenol for the straightforward synthesis of artificial terpenes and functional eugenol derivatives without C=C bond isomerization are described.Résumé -Catalyse de métathèse d'oléfines : une clé pour des transformations d'huiles végétales insaturées et de substances renouvelables -Cet article présente l'importance de la réaction de métathèse croisée des oléfines par catalyse au ruthénium pour la transformation de dérivés de la biomasse en produits utiles pour l'industrie. Il constitue une revue des principaux travaux réalisés dans ce domaine par les auteurs dans leur équipe de catalyse à Rennes (France) en coopération avec l'industrie chimique. La métathèse croisée d'une variété d'oléfines fonctionnelles issues des huiles végétales avec l'acrylonitrile et le fumaronitrile, suivie d'une hydrogénation tandem conduit à des dérivés d'amino acides linéaires, précurseurs de polyamides par polycondensation. L'exploration de la métathèse croisée de nitriles insaturés bio-sourcés avec des acrylates a conduit à des dérivés d'a,x-amino acides, tandis que les aldéhydes gras ont permis un accès rapide à des aldéhydes bifonctionnalisés à longue chaîne et à des diols saturés. Deux voies d'accès à des diènes conjugués fonctionnels impliquant des réactions de métathèse catalysées par le ruthénium à partir d'oléfines issues de la biomasse sont décrites : l'une par métathèse croisée avec un alcyne, l'autre par métathèse croisée avec un chlorure allylique suivie Dedicated to the memory of Yves Chauvin, a great and inspiring pioneer in organometallic catalysis

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Section: Cross-metathesis Of Methyl Ricinoleate With Acrylonitrile Anmentioning

confidence: 99%

“…The 10-undecylenic aldehyde 26 is a renewable derivative obtained from thermal treatment of castor oil [76,77]. Its self-metathesis was attempted to produce the C20 dialdehyde a key intermediate for the production of symmetrical diol or diamine and the formation of polyesters and polyamides.…”

Section: Bifunctional Aldehyde Derivatives Via Self-and Cross-metathementioning

confidence: 99%

Alkene Metathesis Catalysis: A Key for Transformations of Unsaturated Plant Oils and Renewable Derivatives

Dixneuf

Bruneau

Fischmeister

2016

Oil Gas Sci. Technol. – Rev. IFP Energies nouvelles

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“…Undec-10-enoic acid is obtained by pyrolysis of ricinoleic acid, the main component from the fatty acid fraction of castor oil [41]. The cross-metathesis of the corresponding methyl ester bearing a terminal double bond has been investigated with the catalyst precursors 3 and 4 in toluene.…”

Section: Cross-metathesis Of Acrylonitrile With Undec-10enoic Acid Anmentioning

confidence: 99%

Cross‐metathesis with acrylonitrile and applications to fatty acid derivatives

Bruneau

Fischmeister

Miao

et al. 2010

Euro J Lipid Sci & Tech

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International audienceIn this minireview, we report on the state of the art concerning the cross-metathesis of acrylonitrile with olefins. A special focus is given to catalytic conditions that are suitable for medium-size and long-chain aliphatic model substrates. The recent applications of this metathesis reaction to fatty acid derivatives to generate fatty nitriles and bifunctional products are considered. They represent very attractive transformations for the access to N-containing monomers and functional intermediates for the chemical industry from renewable raw materials

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“…The resulting C22 hydroxyketone or acyloin 82 was converted into the a,a,a',a'-tetrachloroeicosadioic acid 83 in five steps (Scheme 19). [82] The conversion of this valuable precursor into Tyromycin A has been elaborated via a Kharasch-type ring closure. [83] Scheme 15.…”

Section: Dimerization Products From Coupling Of the Carboxylic Terminusmentioning

confidence: 99%

Undecylenic Acid: A Valuable and Physiologically Active Renewable Building Block from Castor Oil

2009

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A lot of attention is currently being paid to the transition to a biobased economy. In this movement, most efforts concentrate on the development of bioenergy applications including bioethanol, biodiesel, thermochemical conversion of biomass, and others. However, in the energy sector other nonbiomass alternatives are known, whereas no valuable alternatives are available when thinking about chemical building blocks. Therefore, it is also essential to develop new routes for the synthesis of bio-based chemicals and materials derived thereof. Such intermediates can originate either from plants or from animals. Castor oil is a non-edible oil extracted from the seeds of the castor bean plant Ricinus communis (Euphorbiaceae), which grows in tropical and subtropical areas. Globally, around one million tons of castor seeds are produced every year, the leading producing areas being India, PR China, and Brazil.2 10-Undecenoic acid or undecylenic acid is a fatty acid derived from castor oil that, owing to its bifunctional nature, has many possibilities to develop sustainable applications.

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Undecylenic acid: A valuable renewable building block on route to Tyromycin A derivatives

Cited by 22 publications

References 27 publications

Alkene Metathesis Catalysis: A Key for Transformations of Unsaturated Plant Oils and Renewable Derivatives

Alkene Metathesis Catalysis: A Key for Transformations of Unsaturated Plant Oils and Renewable Derivatives

Cross‐metathesis with acrylonitrile and applications to fatty acid derivatives

Undecylenic Acid: A Valuable and Physiologically Active Renewable Building Block from Castor Oil

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