Relevant bibliographies by topics / Polypropionates

Academic literature on the topic 'Polypropionates'

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Published: 4 June 2021
Last updated: 13 February 2022

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Journal articles on the topic "Polypropionates"

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Blanchfield, JT, DJ Brecknell, IM Brereton, MJ Garson, and DD Jones. "Caloundrin B and Funiculatin A: New Polypropionates From Siphonariid Limpets." Australian Journal of Chemistry 47, no. 12 (1994): 2255. http://dx.doi.org/10.1071/ch9942255.

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Two new polypropionates, caloundrin B (11), systematic name (1″R,2R,3″R,4R,5S,5″R,6S,-7″R,8″S,9″S,10″R)-2-(6′-ethyl-3′,5′-dimethyl-4′-oxopyran-2′-yl)-6-(5″-ethyl-7″-hydroxy-8″,9″,10″-trimethyl-2″,4″,6″-trioxatricyclo[3.3.1.13,7]dec-3″-yl)-5-hydroxy-4-methylheptan-3-one, and funiculatin A (12), systematic name (2ξ,1′S,4R,5′S,6′S)-2-(1′-ethyl-4′,6′,8′-trimethyl-2𔈀,9′-dioxabicyclo[3.3.1]nona-3′,7′-dien-3′-yl)-4,6-dimethylnon-6-en-3-one, have been isolated from Siphonaria zelandica and S. funiculata respectively. The structures of the new compounds were deduced by two-dimensional n.m.r. spectroscopy, particularly long-range 13C- 1H correlation spectroscopy (HMBC), by biosynthetic reasoning and by comparison with the known polypropionates denticulatin A (5), siphonarin B (8), muamvatin (9) and baconipyrone C (14). Information about the relative stereochemistry of the tricyclic ring system of (11) and the bicyclic ring system of (12) was deduced from coupling constant values, and by n.O.e. difference and NOESY experiments, and was confirmed by molecular modelling studies. The relative stereochemistry of the side chains and the absolute stereochemistry were inferred from biosynthetic comparison with the above known polypropionates, and by correlation of funiculatin A with denticulatin A (5) of known absolute stereochemistry. The stereochemistry at C10 of funiculatin A (position 2 of the non-6-en-3-one chain) could not be unambiguously determined. A third new polypropionate funiculatin B, epimeric with funiculatin A at C10, was isolated and partially characterized.
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T. Davies-Coleman, Michael, and Mary J. Garson. "Marine polypropionates." Natural Product Reports 15, no. 5 (1998): 477. http://dx.doi.org/10.1039/a815477y.

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Esposito, Germana, Roberta Teta, Gerardo Della Sala, Joseph Pawlik, Alfonso Mangoni, and Valeria Costantino. "Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea." Marine Drugs 16, no. 8 (August 17, 2018): 285. http://dx.doi.org/10.3390/md16080285.

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The organic extract of the Caribbean sponge Smenospongia aurea has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route such as the smenamides. In this paper, we report the presence of a biogenetically different compound known as smenopyrone, which is a polypropionate containing two γ-pyrone rings. The structure of smenopyrone including its relative and absolute stereochemistry was determined by spectroscopic analysis (NMR, MS, ECD) and supported by a comparison with model compounds from research studies. Pyrone polypropionates are unprecedented in marine sponges but are commonly found in marine mollusks where their biosynthesis by symbiotic bacteria has been hypothesized and at least in one case demonstrated. Since pyrones have recently been recognized as bacterial signaling molecules, we speculate that smenopyrone could mediate inter-kingdom chemical communication between S. aurea and its symbiotic bacteria.
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Davies-Coleman, Michael T., and Mary J. Garson. "ChemInform Abstract: Marine Polypropionates." ChemInform 30, no. 10 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199910319.

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Roke, D., M. Fañanás-Mastral, and B. L. Feringa. "Iterative catalyst controlled diastereodivergent synthesis of polypropionates." Organic Chemistry Frontiers 3, no. 11 (2016): 1383–91. http://dx.doi.org/10.1039/c6qo00199h.

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Carmen Paul, M., Eva Zubía, Maria J. Ortega, and Javier Salvá. "New polypropionates from Siphonaria pectinata." Tetrahedron 53, no. 6 (February 1997): 2303–8. http://dx.doi.org/10.1016/s0040-4020(96)01131-3.

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Ward, Dale E. "The thiopyran route to polypropionates." Chemical Communications 47, no. 41 (2011): 11375. http://dx.doi.org/10.1039/c1cc13323c.

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Zuidema, Daniel R., and Paul B. Jones. "Photochemical Relationships in Sacoglossan Polypropionates." Journal of Natural Products 68, no. 4 (April 2005): 481–86. http://dx.doi.org/10.1021/np049607+.

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Gavagnin, Margherita, Aldo Spinella, Francesco Castelluccio, Guido Cimino, and Arnaldo Marin. "Polypropionates from the Mediterranean Mollusk Elysia timida." Journal of Natural Products 57, no. 2 (February 1994): 298–304. http://dx.doi.org/10.1021/np50104a017.

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Ward, Dale E. "ChemInform Abstract: The Thiopyran Route to Polypropionates." ChemInform 43, no. 3 (December 22, 2011): no. http://dx.doi.org/10.1002/chin.201203259.

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Dissertations / Theses on the topic "Polypropionates"

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Megevand, Sophie. "Etudes sur la synthèse de fragments polypropionates /." [S.l.] : [s.n.], 2000. http://library.epfl.ch/theses/?nr=2271.

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Currie, Russell. "Studies on the total synthesis of non-contiguous polypropionates." Thesis, University of Cambridge, 2013. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.608263.

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Franklin, A. S. "Studies towards the total synthesis of marine derived polypropionates." Thesis, University of Cambridge, 1995. https://www.repository.cam.ac.uk/handle/1810/272999.

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Kernen, Philippe. "Sucres nus de la 2e génération : synthons homochiraux pour les polypropionates /." [S.l.] : [s.n.], 1994. http://library.epfl.ch/theses/?nr=1265.

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Ruiz, Johal. "Nouvelles synthèses par catalyse de composés organosilicés et leur transformation en fragments de polycétides." Thesis, Rennes 1, 2015. http://www.theses.fr/2015REN1S138/document.

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La réaction d'aldolisation est une des méthodes les plus importantes et plus utilisées pour former des liaisons C-C. La réaction tandem d'isomérisation-aldolisation catalytique d'alcools allyliques permet d'effectuer cette réaction avec de nombreux avantages synthétiques et nous avons préparé par ce moyen des beta-hydroxyacylsilanes à partir d'alpha-hydroxyallylsilanes. Tout d'abord, nous avons cherché à mettre au point une version catalytique asymétrique de cette réaction tandem et nous avons aussi synthétisé des beta-hydroxyacylsilanes par aldolisation directe. Ensuite, nous avons utilisé des alpha-hydroxyallylsilanes pour préparer des aldolsalpha-silylés au moyen de réactions d'époxydation. Dans une troisième partie, nous avons synthétisé des aldols à partir de beta-hydroxyacylsilanes protégés de manière simple et efficace, ce qui nous a permis d'effectuer des réactions d'aldolisation itératives. Nous avons illustré le potentiel de cette méthode par la synthèse d'un fragment de (±)-pironetine. Enfin, nous avons synthétisé, à partir des mêmes beta-hydroxyacylsilanes protégés, des éthers d'énol silylés qui ont été ensuite utilisés avec succès comme substrats pour des réactions de Mukaiyama
The aldol reactions is one of the most important and commonly used methods to form C-C bonds. The catalytic tandem isomerization-aldol reaction of allylic alcohols allows to perform this reaction with many synthetic advantages. Thus, we have prepared by this method beta-hydroxyacylsilanes from alpha-hydroxyallylsilanes. First, we have attempted to develop a catalytic asymmetric version of this reaction, and also to synthesize beta-hydroxyacylsilanes by direct aldol reaction. Then, we used alpha-hydroxyallylsilanes to prepare alpha-silyl aldols trough epoxidation reactions. Next, we synthesized aldols from protected beta-hydroxyacylsilanes in a simple and efficient fashion which allowed us to perform iterative aldol reactions. We have illustrated the potential of this method by the synthesis of a fragment of (±)-pironetine. Finally, we have synthesized, from the same protected beta-hydroxyacylsilanes, silyl enol ethers that next have been used successfully as substrates for Mukaiyama aldol reactions
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Jeffery, David William, and david jeffery@awri com au. "Total Synthesis of the Putative Structure of Tridachiahydropyrone." Flinders University. Chemistry, Physics and Earth Science, 2005. http://catalogue.flinders.edu.au./local/adt/public/adt-SFU20050603.095257.

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Polypropionate marine natural products have emerged as a class of compounds that display a high degree of structural diversity. Specifically, metabolites such as that reported as tridachiahydropyrone (7), isolated from sacoglossan molluscs, display novel ring systems. The introductory chapter gives some background on tridachione marine natural products and outlines the isolation of metabolites from several species of sacoglossan mollusc. Chapter One also gives examples of the utility of the tandem conjugate addition-Dieckmann condensation approach being applied to the synthesis of these compounds. Chapter Two describes the development of the tandem conjugate addition-Dieckmann condensation and subsequent trans methylation approach to cyclohexenone rings. The synthetic strategy utilised chiral, functionalised cyclohexenone rings as synthons in the formation of bicyclic ring systems, so development of the carbocyclic ring formation was of vital importance to the overall strategy. Examples are given which confirm the viability of the proposed synthetic route to cyclohexenones such as 91, 92 and 104 from the reaction of [alpha,beta]-unsaturated carbonyl compounds 39 and 59 with dialkyl and dialkenyl Gilman cuprates. Chapter Three describes the incorporation of chiral cyclohexenone 117 into the bicyclic framework of model compound 105, analogous to the marine natural product reported as tridachiahydropyrone (7). The chapter explores the use of cyclohexenone precursor 43 that contained the total carbon framework of the bicyclic core of the desired pyrone. Once again, a tandem conjugate addition-cyclisation reaction was employed using a dialkyl Gilman cuprate, followed by trans methylation to give the requisite cyclohexenone synthon 117. A novel Eaton’s reagent-promoted intramolecular cyclisation of acid 122 to pyrone 123 was then effected. Subsequent O-methylation afforded [alpha]-methoxy-[beta]-methyl-[gamma]-pyrone 105 as a single enantiomer, which had the identical core structure to the natural product. The structure, including relative stereochemistry of 105, was confirmed by single crystal X-ray analysis. Chapter Four builds on the previous two chapters and describes the conjugate addition-cyclisation with a higher order Gilman cuprate derived from vinyl bromide 44, which would deliver the vinyl side-chain required for the synthesis of reported natural product 7. The same acyclic precursor 43 as used in Chapter Three was cyclised and methylated to yield yet another cyclohexenone synthon 41. A single crystal X-ray analysis of related alcohol 162 confirmed the relative stereochemistry and structure. Another novel P2O5-mediated intramolecular cyclisation was achieved to give pyrone 168 and O-methylation provided a compound with the reported structure of natural product 7 as a single enantiomer. The structure of synthetic 7 was established unequivocally through extensive NMR studies. Comparisons of spectral data confirmed that natural tridachiahydropyrone was not the same as synthetic compound 7, so revision of the assigned natural product structure is warranted. Several other analogues were also synthesised using this methodology, highlighting the versatility of the method under development.
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Le, Roux Rémi. "Synthèse biomimétique de motifs polypropionates par hydrogénation asymétrique à l'aide de complexes chiraux du ruthénium. Application aux synthèses du Dolabélide A et du (+)-Discodermolide." Phd thesis, Université Pierre et Marie Curie - Paris VI, 2007. http://pastel.archives-ouvertes.fr/pastel-00003946.

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Ce manuscrit présente le développement d'une méthode de synthèse de motifs polypropionates et son application à la synthèse totale de deux molécules naturelles cytotoxiques : le Dolabélide A et le (+)-Discodermolide. Cette méthode, par analogie avec les voies de biosynthèse des polypropionates, permet la synthèse séquentielle et itérative de ces motifs par l'association de trois réactions : l'hydrogénation asymétrique de béta-cétoesters et de béta-hydroxycétones catalysée par des complexes chiraux du ruthénium, la méthylation diastéréosélective de Fráter-Seebach et la condensation de Claisen. Pour le Dolabélide A, deux fragments avancés ont été préparés, et 7 des 11 centres stéréogènes ont été installés par hydrogénation asymétrique avec des sélectivités supérieures à 95 %. Pour le (+)-Discodermolide, trois fragments intermédiaires ont été élaborés et 10 centres stéréogènes mis en place dont 7 par hydrogénation asymétrique ou méthylation diastéréosélective, ici encore avec des sélectivités supérieures à 95 %.
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Le, Roux Rémi. "Synthèse biomimétique de motifs polypropionates par hydrogénation asymétrique à l'aide de complexes chiraux du ruthénium : application aux synthèses du dolabelide A et du (+)-discodermolide." Paris 6, 2007. https://pastel.archives-ouvertes.fr/pastel-00003946.

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Synthèse biomimétique de motifs polypropionates par hydrogénation asymétrique à l’aide de complexes chiraux du ruthénium. Application aux synthèses du Dolabélide A et du (+) Discodermolide Ce manuscrit présente le développement d’une méthode de synthèse de motifs polypropionates et son application à la synthèse totale de deux molécules naturelles cytotoxiques : le Dolabélide A et le (+)-Discodermolide. Cette méthode, par analogie avec les voies de biosynthèse des polypropionates, permet la synthèse séquentielle et itérative de ces motifs par l’association de trois réactions : l’hydrogénation asymétrique de béta-cétoesters et de béta-hydroxycétones catalysée par des complexes chiraux du ruthénium, la méthylation diastéréosélective de Fráter-Seebach et la condensation de Claisen. Pour le Dolabélide A, deux fragments avancés ont été préparés, et sept des onze centres stéréogènes ont été installés par hydrogénation asymétrique avec des sélectivités supérieures à 95 %. Pour le (+)-Discodermolide, trois fragments intermédiaires ont été élaborés et dix centres stéréogènes mis en place dont sept par hydrogénation asymétrique ou méthylation diastéréosélective, ici encore avec des sélectivités supérieures à 95 %.
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Roche, Christophe. "Approches synthétiques du (+)-discodermolide et du dolabélide A par hydrogénation asymétrique à l'aide de complexes chiraux de ruthénium." Phd thesis, Paris 6, 2008. http://pastel.archives-ouvertes.fr/pastel-00004977.

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L'océan est un vaste réservoir de molécules potentiellement anticancéreuses. Ce manuscrit présente l'approche synthétique de deux molécules naturelles cytotoxiques : le (+)-discodermolide et le dolabélide A. Les motifs polypropionates de ces molécules ont été construits par l'association de trois réactions : la condensation de Claisen pour introduire le motif β-cétoester, l'hydrogénation asymétrique du β-cétoester catalysée par des complexes chiraux de ruthénium puis la méthylation diastéréosélective du β-hydroxyester. Pour le (+)-discodermolide, trois fragments avancés ont été élaborés et 12 des 13 centres stéréogènes mis en place, dont 8 par hydrogénation asymétrique ou méthylation diastéréosélective avec d'excellentes stéréosélectivités. Pour le dolabélide A, deux fragments avancés ont été préparés, et 7 des 8 groupements hydroxyles ont été installés par hydrogénation asymétrique avec des stéréosélectivités supérieures à 95 %.
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Channon, J. A. "A general aldol approach to polypropionate synthesis." Thesis, University of Cambridge, 1992. https://www.repository.cam.ac.uk/handle/1810/272244.

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Books on the topic "Polypropionates"

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Chau, Anh. Diastereoselective palladium-catalyzed formate reduction of allylic carbonates as a route to polypropionate systems. 2004.

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Book chapters on the topic "Polypropionates"

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Ward, Dale E. "Polypropionate Synthesis via Substrate-Controlled Stereoselective Aldol Couplings of Chiral Fragments." In Modern Methods in Stereoselective Aldol Reactions, 377–429. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527656714.ch6.

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