Relevant bibliographies by topics / Tandem conjugate addition-Dieckmann condensation

Academic literature on the topic 'Tandem conjugate addition-Dieckmann condensation'

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Published: 4 June 2021
Last updated: 19 February 2022

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Journal articles on the topic "Tandem conjugate addition-Dieckmann condensation"

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Bunce, Richard A., and Christina R. Harris. "Six-membered cyclic .beta.-keto esters by tandem conjugate addition-Dieckmann condensation reactions." Journal of Organic Chemistry 57, no. 25 (December 1992): 6981–85. http://dx.doi.org/10.1021/jo00051a058.

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Kozhinov, Denis V., and Victor Behar. "Extension of the Tandem Conjugate Addition−Dieckmann Condensation: The Formal Synthesis of Tetracenomycin A2." Journal of Organic Chemistry 69, no. 4 (February 2004): 1378–79. http://dx.doi.org/10.1021/jo035341k.

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BUNCE, R. A., and C. R. HARRIS. "ChemInform Abstract: Six-Membered Cyclic β-Keto Esters by Tandem Conjugate Addition- Dieckmann Condensation Reactions." ChemInform 24, no. 19 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199319129.

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Deville, Jay P., and Victor Behar. "Tandem Conjugate Cyanide Addition−Dieckmann Condensation in the Synthesis of the ABCD-Ring System of Lactonamycin." Organic Letters 4, no. 8 (April 2002): 1403–5. http://dx.doi.org/10.1021/ol0257373.

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Martinez, Aaron D., Jay P. Deville, Joel L. Stevens, and Victor Behar. "Nucleophilic Partners in the Tandem Conjugate Addition−Dieckmann Condensation Reaction: 1. Synthesis of 1,2,3-Trisubstituted Naphthalenes." Journal of Organic Chemistry 69, no. 3 (February 2004): 991–92. http://dx.doi.org/10.1021/jo035342c.

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Zelocualtecatl-Montiel, Iván, Fernando García-Álvarez, Jorge R. Juárez, Laura Orea, Dino Gnecco, Angel Mendoza, Fabrice Chemla, et al. "Asymmetric Tandem Conjugate Addition-Aldol Condensation withN-Acryloyloxazolidines Derived from 2-Phenylglycinol." Asian Journal of Organic Chemistry 6, no. 1 (December 8, 2016): 67–70. http://dx.doi.org/10.1002/ajoc.201600501.

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Talhi, Oualid, Artur Silva, Abdelghani Bouchama, Ridha Hassaine, Nadia Taibi, Ricardo Mendes, Fillipe Almeida Paz, and Khaldoun Bachari. "Diastereoselective One-Pot Tandem Synthesis of Chromenopyridodiazepinones through 1,4- and 1,6-Aza-Conjugate Additions/Heterocyclizations." Synlett 29, no. 07 (January 30, 2018): 885–89. http://dx.doi.org/10.1055/s-0037-1609201.

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We report an efficient one-pot synthesis of a novel series of chromenopyridodiazepinone polyheterocycles by a catalyst-free nucleo­philic addition of ethane-1,2-diamine to (E,E)-3-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-2-styrylchromones at room temperature under mild conditions. The reaction proceeds by a tandem process involving 1,4- and 1,6-aza-conjugate additions of one amino group of ethane-1,2-diamine to the α,β-unsaturated (3-oxoprop-1-en-1-yl) and the α,β,γ,δ-diunsaturated (2-styrylchromone) carbonyl system of the precursor, followed by imine condensation of the remaining amino group to generate the chromenopyridodiazepinone polyheterocycle. All compounds were characterized by means of one- and two-dimensional NMR spectroscopy and single-crystal X-ray crystallography.
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Honda, Takahiro, and Miwako Mori. "Novel Cyclization Reaction by Tandem Michael Addition -Dieckmann Condensation Using Stannyl Anion Generated from Bu3SnSiMe3and F−." Chemistry Letters 23, no. 6 (June 1994): 1013–16. http://dx.doi.org/10.1246/cl.1994.1013.

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Kudirka, Romas A., Robyn M. Barfield, Jesse M. McFarland, Penelope M. Drake, Adam Carlson, Stefanie Bañas, Wes Zmolek, Albert W. Garofalo, and David Rabuka. "Site-Specific Tandem Knoevenagel Condensation–Michael Addition To Generate Antibody–Drug Conjugates." ACS Medicinal Chemistry Letters 7, no. 11 (September 2016): 994–98. http://dx.doi.org/10.1021/acsmedchemlett.6b00253.

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HONDA, T., and M. MORI. "ChemInform Abstract: Novel Cyclization Reaction by Tandem Michael Addition-Dieckmann Condensation Using Stannyl Anion Generated from Bu3SnSiMe3 and F-." ChemInform 25, no. 49 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199449079.

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Dissertations / Theses on the topic "Tandem conjugate addition-Dieckmann condensation"

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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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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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Book chapters on the topic "Tandem conjugate addition-Dieckmann condensation"

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Taber, Douglass F. "Arrays of Stereogenic Centers: The Davies Synthesis of Acosamine." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0041.

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Babak Borhan of Michigan State University found (Angew. Chem. Int. Ed. 2011, 50, 2593) that the ligand developed for asymmetric osmylation worked well for the enantioselective cyclization of 1 to 2. Kyungsoo Oh of IUPUI devised (Org. Lett. 2011, 13, 1306) a Co catalyst for the stereocontrolled addition of 4 to 3 to give 5. Michael J. Krische of the University of Texas Austin prepared (Angew. Chem. Int. Ed. 2011, 50, 3493) 8 by Ir*-mediated oxidation/addition of 7 to 6. Yixin Lu of the National University of Singapore employed (Angew. Chem. Int. Ed. 2011, 50, 1861) an organocatalyst to effect the stereocontrolled addition of 10 to 9. Naoya Kumagai and Masakatsu Shibasaki of the Institute of Microbial Chemistry, Tokyo took advantage (J. Am. Chem. Soc. 2011, 133, 5554) of the soft Lewis basicity of 13 to effect stereocontrolled condensation with 12. Yujiro Hayashi of the Tokyo University of Science found (Angew. Chem. Int. Ed. 2011, 50, 2804, not illustrated) that aqueous chloroacetaldehyde participated well in crossed aldol condensations. Andrew V. Malkov, now at Loughborough University, and Pavel Kocovsky of the University of Glasgow showed (J. Org. Chem. 2011, 76, 4800) that the inexpensive mixed crotyl silane 16 could be added to 15 with high stereocontrol. Shigeki Matsunaga of the University of Tokyo and Professor Shibasaki opened (J. Am. Chem. Soc. 2011, 133, 5791) the meso aziridine 18 with malonate 19 to give 20. Masahiro Terada of Tohoku University effected (Org. Lett. 2011, 13, 2026) the conjugate addition of 22 to 21 with high stereocontrol. Jinxing Ye of the East China University of Science and Technology reported (Angew. Chem. Int. Ed. 2011, 50, 3232, not illustrated) a related conjugate addition. Kian L. Tian of Boston College observed (Org. Lett. 2011, 13, 2686) that the kinetic hydroformylation of 24 set the relative configuration of two stereogenic centers. Alexandre Alexakis and Clément Mazet of the Université de Genève established (Angew. Chem. Int. Ed. 2011, 50, 2354) a tandem one-pot procedure for the addition of 26 to 27 to give 28.
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Taber, Douglass F. "Alkaloid Synthesis: Lycoposerramine Z (Bonjoch), Esermethole (Shishido), Goniomitine (Zhu), Grandisine (Taylor), Reserpine (Jacobsen)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0061.

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Josep Bonjoch of the Universitat de Barcelona extended (Org. Lett. 2013, 15, 326) the Jørgensen variation of the Robinson annulation to the amine-substituted β-keto ester 1. The product cis-fused sulfonamide 3, readily brought to high ee by recrystallization, was carried onto (+)-lycoposerramine Z 4. Intramolecular ketene 2+2 cycloaddition is underdeveloped as a synthetic method. Kozo Shishido of the University of Tokushima observed (Org. Lett. 2013, 15, 200) high diastereoselectivity in the cyclization of 5 to 6. This set the stage for the synthesis of (-)-esermethole 7. Jieping Zhu of the Ecole Polytechnique Fédérale de Lausanne prepared (Angew. Chem. Int. Ed. 2013, 52, 3272) the cyclopentene 8 by coupling the alkenyl triflate with the salt of an α-alkyl arylacetic acid. Ozonolysis followed by reductive work-up led to a diamino keto aldehyde that cyclized to 9. Benzyl ether cleavage delivered (±)-goniomitine 10. Richard J.K. Taylor of the University of York developed (Angew. Chem. Int. Ed. 2013, 52, 1490) a powerful tandem conjugate addition-imination-methanolysis protocol. He had already prepared (+)-grandisine 11 from N-Boc prolinol. Amination-imination converted 11 to (+)-grandisine 12. This was opened by methanolysis to (+)-grandisine G 13. Four diastereomers are possible from the condensation of 14 and 15. Eric N. Jacobsen of Harvard University developed (Org. Lett. 2013, 15, 706) an organocatalyst that delivered 16 as the dominant diastereomer. This was readily converted to (+)-reserpine, the enantiomer of the natural product.
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Taber, Douglass F. "Stereocontrolled Construction of Arrays of Stereogenic Centers: The Mullins Synthesis of (-)-Lasiol." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0045.

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Hisashi Yamamoto of the University of Chicago devised (J. Am. Chem. Soc. 2010, 132, 7878) catalyst systems for the enantioselective epoxidation of a Z -homoallylic alcohol 1. Michael J. Krische of the University of Texas developed (J. Am. Chem. Soc. 2010, 132, 1760) a catalyst system for the highly stereoselective addition of the vinyl acetal 5 to an aldehyde 4. Joëlle Prunet of the University of Glasgow showed (Tetrahedron Lett. 2010, 51, 256) that the tandem cyclization/Julia olefination from 7 also proceeded with high stereocontrol. Professor Yamamoto established (J. Am. Chem. Soc. 2010, 132, 5354) that depending on conditions, the aldol condensation of 10 could be directed selectively toward either diastereomer of the product 12. James M. Takacs of the University of Nebraska effected (J. Am. Chem. Soc. 2010, 132, 1740) the enantioselective hydroboration of 10. The other geometric isomer of 10 gave the alternative diastereomer of 12, also with high ee. John Limanto and Shane W. Krska of Merck Process optimized (Organic Lett . 2010, 12, 512) the dynamic kinetic reduction of 13 , giving 14 with excellent diastereocontrol. Professor Krische extended (J. Am. Chem. Soc. 2010, 132, 4562) his reductive homologation to the (racemic) carbonate 15, delivering 16 with excellent dr and ee. Hirokazu Urabe of the Tokyo Institute of Technology showed (Organic Lett. 2010, 12, 1012) that a Grignard reagent under iron catalysis opened the epoxide 17, readily available by Jørgensen-Cordova epoxidation followed by homologation, with clean inversion and high regiocontrol. Fraser F. Fleming of Duquesne University developed (Organic Lett. 2010, 12, 3030) a general route to quaternary alkylated centers by alkylation of nitriles such as 19. Shigeki Matsunaga and Masakatsu Shibasaki of the University of Tokyo devised (J. Am. Chem. Soc. 2010, 132, 3666) a Ni catalyst for the stereoselective conjugate addition of the lactam 22 to a nitroalkene 21. Aldehydes can also be added to nitroalkenes with high dr and ee, as illustrated by the conversion of 24 to 26 reported (J. Am. Chem. Soc. 2010, 132, 50) by Bukuo Ni of Texas A&M University, Commerce.
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Taber, Douglass F. "Other Methods for Carbocyclic Construction: The Porco Synthesis of (-)-Hyperibone K." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0081.

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Varinder K. Aggarwal of the University of Bristol described (Angew. Chem. Int. Ed. 2010, 49, 6673) the conversion of the Sharpless-derived epoxide 1 into the cyclopropane 2. Christopher D. Bray of Queen Mary University of London established (Chem. Commun. 2010, 46, 5867) that the related conversion of 3 to 5 proceeded with high diastereocontrol. Javier Read de Alaniz of the University of California, Santa Barbara, extended (Angew. Chem. Int. Ed. 2010, 49, 9484) the Piancatelli rearrangement of a furyl carbinol 6 to allow inclusion of an amine 7, to give 8. Issa Yavari of Tarbiat Modares University described (Synlett 2010, 2293) the dimerization of 9 with an amine to give 10. Jeremy E. Wulff of the University of Victoria condensed (J. Org. Chem. 2010, 75, 6312) the dienone 11 with the commercial butadiene sulfone 12 to give the highly substituted cyclopentane 13. Robert M. Williams of Colorado State University showed (Tetrahedron Lett. 2010, 51, 6557) that the condensation of 14 with formaldehyde delivered the cyclopentanone 15 with high diastereocontrol. D. Srinivasa Reddy of Advinus Therapeutics devised (Tetrahedron Lett. 2010, 51, 5291) conditions for the tandem conjugate addition/intramolecular alkylation conversion of 16 to 17. Marie E. Krafft of Florida State University reported (Synlett 2010, 2583) a related intramolecular alkylation protocol. Takao Ikariya of the Tokyo Institute of Technology effected (J. Am. Chem. Soc. 2010, 132, 11414) the enantioselective Ru-mediated hydrogenation of bicyclic imides such as 18. This transformation worked equally well for three-, four-, five-, six-, and seven-membered rings. Stefan France of the Georgia Institute of Technology developed (Org. Lett. 2010, 12, 5684) a catalytic protocol for the homo-Nazarov rearrangement of the doubly activated cyclopropane 20 to the cyclohexanone 21. Richard P. Hsung of the University of Wisconsin effected (Org. Lett. 2010, 12, 5768) the highly diastereoselective rearrangement of the triene 22 to the cyclohexadiene 23. Strategies for polycyclic construction are also important. Sylvain Canesi of the Université de Québec devised (Org. Lett. 2010, 12, 4368) the oxidative cyclization of 24 to 25.
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