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Relevant bibliographies by topics / Syntheses of cyclopentenones

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Academic literature on the topic 'Syntheses of cyclopentenones'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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Journal articles on the topic "Syntheses of cyclopentenones"

1

Mikołajczyk, Marian. "Phosphonate reagents and building blocks in the synthesis of bioactive compounds, natural products and medicines." Pure and Applied Chemistry 91, no. 5 (2019): 811–38. http://dx.doi.org/10.1515/pac-2018-1117.

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Abstract This account outlines the results obtained in the author’s laboratory on the application of phosphonates in the synthesis of various classes of biologically active cyclopentenones and cyclopentanones. In the first place two general methods for the synthesis of mono-, 1,2- and 1,4-dicarbonyl compounds are presented. The first is based on the use of α-phosphoryl sulfides in conjunction with the Horner reaction while in the second method the oxygenation reaction of α-phosphonate carbanion is a key step. The utility of these two approaches to 1,4-diketones as precursors of cyclopentenones

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Li, Ertong, Changwei Li, Jing Wang, et al. "Lewis acid-catalyzed tandem acylation–Nazarov cyclization for the syntheses of fused cyclopentenones." Tetrahedron 70, no. 4 (2014): 874–79. http://dx.doi.org/10.1016/j.tet.2013.12.025.

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Rao, Maddali Lakshmi Narayana, and Mariappan Periasamy. "Novel Syntheses of Cyclopentenones and Alkenylsilanes from the Corresponding Alkyne−Dicobalt Hexacarbonyl Complexes." Organometallics 15, no. 1 (1996): 442–45. http://dx.doi.org/10.1021/om950185w.

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Chomcheon, Porntep, Nongluksna Sriubolmas, Suthep Wiyakrutta, et al. "Cyclopentenones, Scaffolds for Organic Syntheses Produced by the Endophytic Fungus Mitosporic Dothideomycete sp. LRUB20." Journal of Natural Products 69, no. 9 (2006): 1351–53. http://dx.doi.org/10.1021/np060148h.

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RAO, M. L. N., and M. PERIASAMY. "ChemInform Abstract: Novel Syntheses of Cyclopentenones and Alkenylsilanes from the Corresponding Alkyne-Dicobalt Hexacarbonyl Complexes." ChemInform 27, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199618071.

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Li, Ertong, Changwei Li, Jing Wang, et al. "ChemInform Abstract: Lewis Acid-Catalyzed Tandem Acylation-Nazarov Cyclization for the Syntheses of Fused Cyclopentenones." ChemInform 45, no. 29 (2014): no. http://dx.doi.org/10.1002/chin.201429139.

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Lvov, Andrey G., Alexey V. Zakharov, Konstantin A. Lyssenko, Vadim V. Kachala, and Valerii Z. Shirinian. "Dialkylation of Ethyl 4-(Het)aryl-3-oxobutanoates as a Route to 5-(2-Oxoethyl)cyclopentenones." Synlett 30, no. 11 (2019): 1321–23. http://dx.doi.org/10.1055/s-0039-1689926.

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An unexplored ability of the long-known chemical transformation, Borsche’s cyclopentenone synthesis (the construction of a 1,4-diketone with subsequent base-induced cyclization), is reported. Double alkylation of ethyl 4-(het)aryl-3-oxobutanoates with 2-bromo-1-(het)arylethanones, with subsequent alkali treatment, provides access to cyclopentenones substituted with a 2-oxoethyl group at the 5-position. These products might serve as valuable synthons for heterocyclization, and this feature was demonstrated by synthesis of 4H-cyclopenta[b]thiophene derivatives.

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Jenkins, Aireal D., Ananda Herath, Minsoo Song, and John Montgomery. "Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition." Journal of the American Chemical Society 133, no. 36 (2011): 14460–66. http://dx.doi.org/10.1021/ja206722t.

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Hailes, Helen C., Ben Isaac та M. Hashim Javaid. "1,4-Addition of chiral 2-propenylphosphonamide anions to α-substituted cyclopentenones: use in enantioselective syntheses of methyl dihydrojasmonates and methyl jasmonates". Tetrahedron Letters 42, № 41 (2001): 7325–28. http://dx.doi.org/10.1016/s0040-4039(01)01437-x.

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Gowala, Tarak N., Pankaj Chaudhari, Jagadish Pabba, Krishna Sawant, Sitaram Pal, and Sujit K. Ghorai. "Synthesis of 2,3,4-Trisubstituted 2-Cyclopentenones via Sequential Functionalization of 2-Cyclopentenone." Journal of Organic Chemistry 86, no. 15 (2021): 10812–18. http://dx.doi.org/10.1021/acs.joc.1c01039.

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Dissertations / Theses on the topic "Syntheses of cyclopentenones"

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Casey, G. "Ramberg-Baecklund reactions of thian-4-one derivatives." Thesis, University of East Anglia, 1987. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.382863.

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Yang, Jiong. "The total syntheses of jatrophatrione, citlalitrione, and sclerophytin A studes toward the enantioselective synthesis of fomannosin; photochemical rearrangement of 4-methoxy-4-vinyl-2-cyclopentenones /." Columbus, Ohio : Ohio State University, 2003. http://rave.ohiolink.edu/etdc/view?acc%5num=osu1062130125.

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Thesis (Ph. D.)--Ohio State University, 2003.<br>Title from first page of PDF file. Document formatted into pages; contains xx, 293 p. : ill. Advisor: Leo A. Paquette, Department of Chemistry. Includes bibliographical references (p. 88-101).

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Yang, Jiong. "The total syntheses of jatrophatrione, citlalitrione, and sclerophytin A; Studies toward the enantioselective synthesis of fomannosin; Photochemical rearrangement of 4-methoxy-4-vinyl-2-cyclopentenones." The Ohio State University, 2003. http://rave.ohiolink.edu/etdc/view?acc_num=osu1062130125.

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Tumay, Tulay Asli. "Synthesis Of Ferrocenyl Cyclopentenones." Master's thesis, METU, 2005. http://etd.lib.metu.edu.tr/upload/3/12606372/index.pdf.

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ABSTRACT SYNTHESIS OF FERROCENYL CYCLOPENTENONES TUMAY, T&uuml<br>lay Asli M.S., Department of Chemistry Supervisor: Assoc. Prof. Dr. Metin Zora August 2005, 80 pages Construction of highly functionalized five-membered rings via cycloaddition reaction of cyclopropylcarbene-chromium complex with alkynes has become a very active area of research in recent years by virtue of their presence in antitumour natural products. Also with the finding that ferrocene derivatives are active against various tumours, considerable interest has been devoted to the synthesis of new ferrocene derivatives

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Iqbal, Mazhar. "Synthesis of biologically important cyclopentenones." Thesis, University of Liverpool, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.420456.

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Cheung, Steven. "Novel synthesis of polyfunctional cyclopentenones." Thesis, University of Sussex, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.391831.

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MeÌnard, Morgan. "Asymmetric synthesis of substituted cyclopentenone derivatives." Thesis, University of Oxford, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.398286.

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Etheridge, Zac C. "Studies towards the synthesis of neocarzinostatin chromophore." Thesis, University of Sussex, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.288634.

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Rettie, Alan Bruce. "Use of organometallic complexes for the synthesis of condensed cyclopentenones." Thesis, Heriot-Watt University, 1991. http://hdl.handle.net/10399/1029.

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Burke, Mark Richard. "The use of cyclopentenones in the synthesis of novel carbocycles." Thesis, Queen's University Belfast, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.486045.

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4-Substituted cyclopentenones are key intermediates in the preparation of an array of highly functionalised cyclopentanes including most importantly in the project, carbocyclic nucleosides which display interesting biological activity. With the discovery that one stereoisomer exhibits generally more biological activity than the opposite stereoisomer and the escalating demand for new drugs to be enantiomerically pure, has led to the principal use ofenzymes in the development of routes to chiral carbocyclic nucleosides. The 1,4-diacetate was prepared via 3,4-diacetoh.)'cyclopentene using a modif

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Books on the topic "Syntheses of cyclopentenones"

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Jeffrey, Stephen. The use of Thian-4-one derivatives in cyclopentenone natural product synthesis. University ofEast Anglia, 1990.

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Book chapters on the topic "Syntheses of cyclopentenones"

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Li, Jie Jack. "Pauson-Khand cyclopentenone synthesis." In Name Reactions. Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_213.

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Li, Jie Jack. "Pauson-Khand cyclopentenone synthesis." In Name Reactions. Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_224.

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Pauson, P. L. "Cyclopentenone Formation from Alkyne-Cobalt Complexes." In Organometallics in Organic Synthesis. Springer Berlin Heidelberg, 1987. http://dx.doi.org/10.1007/978-3-642-73196-9_12.

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4

Taber, Douglass F. "Organocatalyzed Carbocyclic Construction: (+)-Roseophilin (Flynn) and (+)-Galbulin (Hong)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0071.

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Armido Studer of Wilhems-University Münster effected (Chem. Commun. 2012, 48, 5190) the enantioselective conjugate addition of 2 to 1, leading to the cyclopropane 3. Karl Anker Jørgensen of Aarhus University devised (J. Am. Chem. Soc. 2012, 134, 2543) a route to cyclobutanes based on the enantioselective addition of 5 to the nitroalkene 4. Jose L. Vicario of the Universidad del País Vasco reported (Angew. Chem. Int. Ed. 2012, 51, 4104) a similar procedure. Benjamin List of the Max-Planck-Institute Mülheim epoxidized (Adv. Synth. Catal. 2012, 354, 1701) cyclopentenones such as 7 with high ee. Lutz H. Gade of the Universität Heidelberg observed (J. Am. Chem. Soc. 2012, 134, 2946) high ee in the benzylation of 9. Cheng Ma of Zhejiang University formylated (J. Org. Chem. 2012, 77, 2959) cyclopentanone, then condensed the resulting aldehyde 12 with 13 to give 14. Hao Xu of Georgia State University cyclized (Org. Lett. 2012, 14, 858) 15 to the cyclopentenone 16. (+)-Rosephilin 19 inhibits several phosphatases. Bernard L. Flynn of Monash University prepared (Org. Lett. 2012, 14, 1740) the carbocyclic core of 19 by cyclizing 17 to the cyclopentenone 18. Masanori Yoshida of Hokkaido University designed (J. Org. Chem. 2011, 76, 8513) a very simple organocatalyst for the enantioselective conjugate addition of 21 to 20. Samuel H. Gellman of the University of Wisconsin showed (Org. Lett. 2012, 14, 2582) that nitromethane could be added to 23 with high ee. Hiroaki Sasai of Osaka University effected (Angew. Chem. Int. Ed. 2012, 51, 5423) the enantioselective cyclization of the prochiral 25. Ying-Chun Chen of Sichuan University found (Angew. Chem. Int. Ed. 2012, 51, 4401) that the diene 27 could be converted to 29 by way of the intermediate trienamine. Bor-Cherng Hong of the National Chung Cheng University observed (Chem. Commun. 2012, 48, 2385) that under organocatalysis, only one enantiomer of 31 would add to 30, delivering 32 in high ee. Aromatization of 32 led to (+)-galbulin 33.

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Merino, P. "Synthesis from Cyclopentenones and Related Compounds." In Monocyclic Arenes, Quasiarenes, and Annulenes. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-045-00089.

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Choe, Jachoon, Youngwoon Kwon, Jong-Ku Lee, and Kwang Ho Song. "Continuous cyclopentenone synthesis with static mixer reactor." In New Developments and Application in Chemical Reaction Engineering. Elsevier, 2006. http://dx.doi.org/10.1016/s0167-2991(06)81720-9.

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7

Taber, Douglass F. "Metal-Mediated Carbocyclic Construction: The Simpkins Synthesis of Ialibinones A and B." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0075.

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Adriaan J. Minnaard and Ben L. Feringa of the University of Groningen devised (J. Am. Chem. Soc. 2010, 132, 14349) what promises to be a general strategy for the construction of enantiomerically pure cyclopropanes, based on conjugate addition to acceptors such as 1 . X. Peter Zhang of the University of South Florida developed (J. Am. Chem. Soc. 2010, 132, 12796) a Co catalyst for the enantioselective cyclopropanation of α-olefins such as 3. Seiji Iwasa of Toyohashi University of Technology designed (Angew. Chem. Int. Ed. 2010, 49, 8439) a resin-bound Ru catalyst that could be used repeatedly for the enantioselective cyclization of the ester 6. Rai-Shung Lin of National Tsing-Hua University showed (Angew. Chem. Int. Ed. 2010, 49, 9891) that a gold catalyst could expand the alkyne 8 to the cyclobutene 9. Takao Ikariya of the Tokyo Institute of Technology reported (J. Am. Chem. Soc. 2010, 132, 16637) a detailed study of the enantioselective conjugate addition of malonate 11 to cyclopentenone 10. Vladimir A. D’yakonov of the Russian Academy of Sciences, Ufa, showed (Tetrahedron Lett. 2010, 51, 5886) that a cyclic alkyne 13 could be annulated to the cyclopentenone 14. Shunichi Hashimoto of Hokkaido University also designed (Angew. Chem. Int. Ed. 2010, 49, 6979) a resin-bound Rh catalyst that could also be used repeatedly for the enantioselective cyclization of the ester 15. Tushar Kanti Chakraborty of the Central Drug Research Institute used (Tetrahedron Lett. 2010, 51, 4425) Ti(III) to mediate the diastereoselective cyclization of 17 to 18. Alexandre Alexakis of the University of Geneva extended (Synlett 2010, 1694) enantioselective conjugate addition of isopropenyl to the more difficult enone 19. Joseph P. A. Harrity of the University of Sheffield showed (Org. Lett. 2010, 12, 4832) that Pd could catalyze the rearrangement of 21 to 22. Strategies for the controlled construction of polycyclic ring systems are also important. Günter Helmchen of the Universität Heidelberg showed (J. Org. Chem. 2010, 75, 7917) that 23 was efficiently cyclized to the diene with Pt catalyst. The reaction could be carried out in the presence of the dienophile 24 to give 25 directly.

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Taber, Douglass. "Stereocontrolled Carbocyclic Construction: (-)-Mintlactone (Bates), (-)-Gleenol (Kobayashi), (-)-Vibralactone C (Snider)." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0081.

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Nigel S. Simpkins, now at the University of Birmingham, found (Chem. Commun. 2008, 5390) that the prochiral cyclopropane amide 1 could be deprotonated to give, after alkylation, the substituted cyclopropane 3 with high enanantio- and diastereocontrol. In the course of a synthesis of (+)-Lineatin, Ramon Alibés of the Universitat Autònoma de Barcelona optimized (J. Org. Chem. 2008, 73, 5944) the photochemical cycloaddition of 4 and 5 to give, after reductive dechlorination, the cyclobutene 6. In a related reaction, José L. García Ruano and M. Rosario Martín of the Universidad Autónoma de Madrid observed (J. Org. Chem. 2008, 73, 9366) that the cycloaddition of 8 to 7 proceeded with high regio- and diastereocontrol, to give the cyclopentene 9. Joseph M. Ready of UT Southwestern in Dallas developed (Angew. Chem. Int. Ed. 2008, 47, 7068) a powerful new cyclopentannulation, condensing the cyclopropane derived from the addition of 11 to 10 with the protected ynolate 12 to give 13, in the presence of a modified Lewis acid catalyst. Chun-Chen Liao of the National Tsing Hua University, Hsinchu described (Angew. Chem. Int. Ed. 2008, 47, 7325) the oxidative ring contraction of the o-alkoxy phenol 14 to the cyclopentenone 15. Stéphane Quideau of the Université de Bordeaux reported (Organic Lett. 2008, 10, 5211) a related ring contraction. We uncovered (J. Org. Chem. 2008, 73, 9479) a simple protocol for the in situ conversion of an ω-alkenyl ketone such as 16 to the corresponding diazo compound, leading, via dipolar cycloaddition, to the adduct 17. Ulrich Zutter of Roche Basel described (J. Org. Chem. 2008 , 73, 4895), in a synthesis of Tamiflu, the hydrogenation of 19 to give the cyclohexane with all-cis diastereocontrol. Selective removal of the methyl ethers with trimethylsilyl iodide set the stage for enzymatic ester hydrolysis, delivering 20 in high ee.

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9

Taber, Douglass F. "Alkaloid Synthesis: (–)-α-Kainic Acid (Cohen), Hyacinthacine A2 (Fox), (–)-Agelastatin A (Hamada), (+)-Luciduline (Barbe), (+)-Lunarine (Fan), (–)-Runanine (Herzon)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0058.

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The intramolecular ene cyclization is still little used in organic synthesis. Theodore Cohen of the University of Pittsburgh trapped (J. Org. Chem. 2011, 76, 7912) the cyclization product from 1 with iodine to give 2, setting the stage for an enantiospecific total synthesis of (–)-α-kainic acid 3. Intramolecular alkene hydroamination has been effected with transition metal catalysts. Joseph M. Fox of the University of Delaware isomerized (Chem. Sci. 2011, 2, 2162) 4 to the trans cyclooctene 5 with high diastereocontrol. Deprotection of the amine led to spontaneous cyclization, again with high diastereocontrol to hyacinthacine A2 6. Yasumasa Hamada of Chiba University devised (Org. Lett. 2011, 13, 5744) a catalyst system for the enantioselective aziridination of cyclopentenone 7. The product 8 was carried on to the tricyclic alkaloid (–)-agelastatin A 9. Guillaume Barbe, now at Novartis in Cambridge, MA, effected (J. Org. Chem. 2011, 76, 5354) the enantioselective Diels-Alder cycloaddition of acrolein 11 to the dihydropyridine 10. Ring-opening ring-closing metathesis later formed one of the carbocyclic rings of (+)-luciduline 13, and set the stage for an intramolecular aldol condensation to form the other. Chun-An Fan of Lanzhou University employed (Angew. Chem. Int. Ed. 2011, 50, 8161) a Cinchona-derived catalyst for the enantioselective Michael addition to prepare 14. Although 14 and 15 were only prepared in 77% ee, crystallization to remove the racemic component of a later intermediate led to (+)-lunarine 16 in high ee. Seth B. Herzon of Yale University used (Angew. Chem. Int. Ed. 2011, 50, 8863) the enantioselective Diels-Alder addition with 18 to block one face of the quinone 17. Reduction of 19 followed by methylation delivered an iminium salt, only one face of which was open for the addition of an aryl acetylide. Thermolysis to remove the cyclopentadiene gave an intermediate that was carried on to (+)-runanine 20.

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10

Taber, Douglass F. "Diels-Alder Cycloaddition: (+)-Armillarivin (Banwell), Gelsemiol (Gademann), (+)-Frullanolide (Liao), Myceliothermophin A (Uchiro), Peribysin E (Reddy), Caribenol A (Li/Yang)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0081.

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Martin G. Banwell of the Australian National University prepared (Org. Lett. 2013, 15, 1934) the enantiomerically pure diol 1 by fermentation of the aromatic precursor. Diels-Alder addition of cyclopentenone 2 proceeded well at elevated pressure to give 3, the precursor to (+)-armillarivin 4. Karl Gademann of the University of Basel found (Chem. Eur. J. 2013, 19, 2589) that the Diels-Alder addition of 6 to 5 proceeded best without solvent and with Cu catalysis to give 7. Reduction under free radical conditions led to gelsemiol 8. Chun-Chen Liao of the National TsingHua University carried out (Org. Lett. 2013, 15, 1584) the diastereoselective addition of 10 to 9. A later oxy-Cope rearrangement established the octalin skeleton of (+)-frullanolide 12. D. Srinivasa Reddy of CSIR-National Chemical Laboratory devised (Org. Lett. 2013, 15, 1894) a strategy for the construction of the angularly substituted cis-fused aldehyde 15 based on Diels-Alder cycloaddition of 14 to the diene 13. Further transformation led to racemic peribysin-E 16. An effective enantioselective catalyst for dienophiles such as 14 has not yet been developed. Hiromi Uchiro of the Tokyo University of Science prepared (Tetrahedron Lett. 2012, 53, 5167) the bicyclic core of myceliothermophin A 19 by BF3•Et2O-promoted cyclization of the tetraene 17. The single ternary center of 17 mediated the formation of the three new stereogenic centers of 18, including the angular substitution. En route to caribenol A 22, Chuang-Chuang Li and Zhen Yang of the Peking University Shenzen Graduate School assembled (J. Org. Chem. 2013, 78, 5492) the triene 20 from two enantiomerically pure precursors. Inclusion of the radical inhibitor BHT sufficed to suppress competing polymerization, allowing clean cyclization to 21. Methylene blue has also been used (J. Am. Chem. Soc. 1980, 102, 5088) for this purpose.

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Conference papers on the topic "Syntheses of cyclopentenones"

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Filho, Luis Gustavo de Sousa, and Fernando Coelho. "AN APPROACH TO THE SYNTHESIS OF SUBSTITUTED CYCLOPENTENONES WITH POTENTIAL ANTI-INFLAMMATORY ACTIVITY FROM MORITA-BAYLIS-HILLMAN ADDUCT." In 14th Brazilian Meeting on Organic Synthesis. Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0255-1.

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