Relevant bibliographies by topics / Dieckmann condensation

Academic literature on the topic 'Dieckmann condensation'

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Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Dieckmann condensation"

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Maklad, Noha S. "ChemInform Abstract: Dieckmann Condensation." ChemInform 42, no. 18 (April 7, 2011): no. http://dx.doi.org/10.1002/chin.201118225.

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Pátek, Marcel. "Titanium-mediated Dieckmann condensation." Collection of Czechoslovak Chemical Communications 55, no. 5 (1990): 1223–27. http://dx.doi.org/10.1135/cccc19901223.

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The Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)-benzoates Ia and Ib with titanium tetrachloride-tert-amine or butyltitanium ate complex III affords alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides IIa and IIb which are the piroxicam intermediates.
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Sieburth, Scott McN, and Chien-An Chen. "Tandem Asymmetric Alkylation-Dieckmann Condensation." Synlett 1995, no. 09 (September 1995): 928–30. http://dx.doi.org/10.1055/s-1995-5131.

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Nishimura, Tamiki, Makoto Sunagawa, Toshiya Okajima, and Yoshimasa Fukazawa. "Transition structures for the dieckmann condensation." Tetrahedron Letters 38, no. 40 (October 1997): 7063–66. http://dx.doi.org/10.1016/s0040-4039(97)01649-3.

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SIEBURTH, S. M., and C. A. CHEN. "ChemInform Abstract: Tandem Asymmetric Alkylation-Dieckmann Condensation." ChemInform 27, no. 3 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199603179.

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Pátek, Marcel, and František Hampl. "Conditions of the Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)benzoates." Collection of Czechoslovak Chemical Communications 54, no. 12 (1989): 3267–77. http://dx.doi.org/10.1135/cccc19893267.

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The Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)benzoates IIIa-IIIe with various bases affords alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides IVa-IVe which are intermediates in the synthesis of antiinflammatory drug piroxicam. The yields of benzothiazines IVa-IVe depend mostly on the nature of a base, reaction temperature and solvent used for these condensations. Hitherto undescribed esters IIIb-IIIe were synthesized and their structures were confirmed by 1H and 13C NMR, and mass spectra.
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Böhme, Roswitha, Günther Jung, and Eberhard Breitmaier. "Synthesis of the Antibiotic (R)-Reutericyclinvia Dieckmann Condensation." Helvetica Chimica Acta 88, no. 11 (November 2005): 2837–41. http://dx.doi.org/10.1002/hlca.200590226.

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Chande, Madhukar S., Rahul R. Khanwelkar, and Pravin A. Barve. "Synthesis of Novel Spiro Compounds using Anthrone and Pyrazole-5-thione Moieties: A Michael Addition approach." Journal of Chemical Research 2007, no. 8 (August 2007): 468–71. http://dx.doi.org/10.3184/030823407x237821.

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Novel routes for the synthesis of spiro derivatives anthrone have been designed using a Michael addition reaction followed by a Dieckmann condensation and Thorpe–Ziegler cyclisation. Bis-Michael addition of pyrazole-5-thione with 1,5-diarylpenta-1,4-dien-3-one gave directly a spiro derivative of pyrazole-5-thione. An enol lactone was synthesised by using mono Michael addition on dimedone, followed by hydrolysis and condensation.
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Lei, Jie, Gui-Ting Song, Ya-Fei Luo, Dian-Yong Tang, Wei Yan, Hong-yu Li, Zhong-Zhu Chen, and Zhi-Gang Xu. "Synthesis of indoline-piperidinones via a novel Ugi, ring expansion, pseudo-Dieckmann condensation and rearrangement cascade reaction." Organic Chemistry Frontiers 7, no. 5 (2020): 737–41. http://dx.doi.org/10.1039/d0qo00028k.

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Iskakova, M. M., I. M. Biktagirov, L. Kh Faizullina, Sh M. Salikhov, M. G. Safarov, and F. A. Valeev. "Regiocontrolled dieckmann condensation of 3,4-Bis(methoxycarbonylmethyl) levoglucosenone derivative." Russian Journal of Organic Chemistry 50, no. 1 (January 2014): 105–9. http://dx.doi.org/10.1134/s1070428014010205.

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Dissertations / Theses on the topic "Dieckmann condensation"

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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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Kasprzyk, Milena, and milena kasprzyk@freehills com. "Synthetic Studies Towards the Tridachione Family of Marine Natural Products." Flinders University. Chemistry, Physics and Earth Sciences, 2008. http://catalogue.flinders.edu.au./local/adt/public/adt-SFU20081107.085933.

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Since the middle of the 20th century, significant interest has evolved from the scientific community towards the polypropionate family of marine natural products. A number of these compounds have been shown to possess significant biological activity, and this property, as well as their structural complexity, has driven numerous efforts towards their synthesis. The first chapter provides an introduction into the world of polypropionates, with a discussion on synthetic studies into a number of members of the tridachiapyrone family. Fundamental synthetic concepts utilised in this thesis towards the preparation of polyketides are also described, with a focus on their application towards the synthesis of 9,10-deoxytridachione, anti tridachiahydropyrone and syn tridachiahydropyrone. Chapter 2 describes the work undertaken towards the total synthesis of 9,10-deoxytridachione. The novel tandem conjugate addition-Dieckmann condensation of complex enones developed previously in the Perkins group was used to generate anti methylated cyclohexenones as key synthetic intermediates. The conversion of the cyclohexenones into the corresponding cyclohexadienes via allylic alcohols was attempted, utilising a Grignard-mediated reaction to achieve the selective 1,2-reduction. Studies into the Grignard-mediated reduction were also undertaken on seven additional cyclohexenones, in order to investigate the utility and scope of the reaction. The extension of the methodology previously developed for the synthesis of cyclohexenones is the subject of Chapter 3. This section describes investigations into the synthesis of stereochemically-diverse cyclohexenones from complex enones. The conjugate addition-Dieckmann condensation strategy was extended successfully towards the synthesis of a syn methylated cyclohexenone, which allowed the synthesis of the proposed true structure of tridachiahydropyrone to be pursued. The methodology developed in Chapter 3 was utilised in Chapter 4 to synthesise a model system of syn tridachiahydropyrone. A comparative analysis of the NMR data of the syn model, an anti model and anti tridachiahydropyrone with the natural product indicated that the true structure of tridachiahydropyrone may indeed have syn stereochemistry. The synthesis of syn tridachiahydropyrone was attempted, and to this end a suitable cyclohexanone was successfully synthesised. However, the subsequent methylation-elimination cascade failed to furnish the desired syn methylated cyclohexenone, producing only an anti methylated cyclohexanone. The stereochemistry of the methylation was deduced using high and low variable temperature NMR coupled with selective irradiation NOESY.
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Mallinger, Aurélie. "Synthèse de dérivés de l'acide tétronique et de l'acide pulvinique." Phd thesis, Paris 11, 2008. http://www.theses.fr/2008PA112259.

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Plusieurs pigments de champignons, tels que la norbadione A et des dérivés de l'acide pulvinique, ont révélé une activité antioxydante remarquable. Au cours de cette thèse, nous nous sommes intéressés à la synthèse de ces composés qui pourraient être employés comme agents de protection contre les rayonnements ionisants. Dans ce contexte, une nouvelle voie d'accès à des dérivés de l'acide tétronique a été mise au point à partir d'arylacétates de méthyle et d'hydroxyesters. La méthodologie développée a permis, en une seule étape, la synthèse de plusieurs acides 3-aryltétroniques et de composés hétérocycliques apparentés. A partir d'un dérivé de l'acide tétronique, trois esters d’acides pulviniques naturels ont été préparés par une voie très directe et avec de bons rendements. Dans le cadre de la synthèse totale de la norbadione A, deux voies de synthèse ont été étudiées. La première consiste à appliquer la méthodologie développée au cours de cette thèse pour la synthèse d’acides pulviniques. Les travaux réalisés ont ainsi permis la synthèse d'un intermédiaire avancé. La seconde voie, dont l’étape clé est un double couplage de Suzuki-Miyaura, a conduit à la première synthèse totale de la norbadione A
Several mushrooms pigments, such as norbadione A and pulvinic acid derivatives, exhibit a remarkable antioxidant activity. In the course of this PhD thesis, we have been interested in the synthesis of these compounds, which could be used as protection agents against ionizing radiations. In this context, a novel access to tetronic acid derivatives has been developed from methyl arylacetates and hydroxyesters. The methodology allows the synthesis of several 3-aryltetronic acids and related heterocyclic compounds in one step. From one of these tetronic acid derivatives, three natural esters of pulvinic acids have been prepared straightforwardly and in good yields. With regards to norbadione A total synthesis, two routes have been envisioned. The first one consists in the application of the methodology developed for the synthesis of pulvinic acids. This work has allowed us to synthesise a key bis(tetronic) intermediate. The second route, for which the key step is a double Suzuki-Miyaura cross-coupling, has allowed to complete the first total synthesis of norbadione A
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Book chapters on the topic "Dieckmann condensation"

1

Li, Jie Jack. "Dieckmann condensation." In Name Reactions, 110. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_86.

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Li, Jie Jack. "Dieckmann condensation." In Name Reactions, 97. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_81.

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Li, Jie Jack. "Dieckmann condensation." In Name Reactions, 182–83. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_79.

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4

Li, Jie Jack. "Dieckmann condensation." In Name Reactions, 209–10. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_87.

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Li, Jie Jack. "Dieckmann Condensation." In Name Reactions, 162–65. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_44.

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6

Chataigner, I., A. Harrison-Marchand, and J. Maddaluno. "Dieckmann Condensation." In Ketones, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-026-01127.

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7

Rayner, C. M., and M. A. Graham. "Dieckmann Condensation." In Fused Five-Membered Hetarenes with One Heteroatom, 1. Georg Thieme Verlag KG, 2001. http://dx.doi.org/10.1055/sos-sd-010-00219.

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Segi, M. "By Dieckmann Condensation." In Sulfur, Selenium, and Tellurium, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-039-01047.

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9

Taber, Douglass F. "The Li Synthesis of (–)-Fusarisetin A." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0097.

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Fusarisetin A 3 is an intriguing inhibitor of cell migration and invasion that is not itself cytotoxic. Ang Li of the Shanghai Institute of Organic Chemistry developed (J. Am. Chem. Soc. 2012, 134, 920) a total synthesis of (–)-fusarisetin A, demonstrating that the natural material had the absolute configuration opposite to that originally assigned. A key step in the synthesis was the highly diastereoselective cyclization of 1 to 2. The absolute configuration of 1 and so of synthetic 3 was derived from commercial citronellol, which is prepared on an industrial scale by asymmetric synthesis. To this end, the reagents 6 and 8 were required. The β-ketothio ester 6 was prepared from the Meldrum’s acid 4 and the phosphonate 8 was derived from methyl sorbate 7. The acetal of citronellal 9 was ozonized with reductive work-up to give the alcohol 10. Protection followed by hydrolysis gave the aldehyde 11, which was condensed with 8 to give the triene 12. Deprotection followed by oxidation delivered an aldehyde, which was condensed with 6 to give the Diels-Alder precursor 1. With BF3 • OEt2 catalysis, the Diels-Alder cycloaddition proceeded under mild conditions, –40oC for 40 min, leading to 2 as a single diastereomer. Comparable intramolecular Diels-Alder cyclizations with single carbonyl activation gave mixtures of diastereomers. The alcohol 13 was prepared by transesterification of 2 with trifluoroethanol. Activation with MsCl led directly to the kinetic O-alkylation product 14. Following the precedent of Trost (J. Am. Chem. Soc. 1980, 102, 2840), exposure to a Pd catalyst smoothly converted 14 into 15 as the desired diastereomer. Condensation of the ester 15 with the amine 16 gave the diene 17. Selective oxidation of the monosubstituted alkene under Wacker conditions gave the ketone, which was reduced selectively by the Luche protocol to the alcohol 18. Exposure of 18 to NaOCH3 initiated Dieckmann cyclization, leading to (–)-fusarisetin A 3.
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