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Journal articles on the topic 'Syntheses of cyclopentenones'

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Published: 4 June 2021

Last updated: 10 February 2022

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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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Zhou, Rong, Kai Zhang, Ling Han, Yusong Chen, Ruifeng Li, and Zhengjie He. "Unusual Formal [1+4] Annulation through Tandem P(NMe2 )3 -Mediated Cyclopropanation/Base-Catalyzed Cyclopropane Rearrangement: Facile Syntheses of Cyclopentenimines and Cyclopentenones." Chemistry - A European Journal 22, no. 17 (2016): 5883–87. http://dx.doi.org/10.1002/chem.201505047.

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12

Jenkins, Aireal D., Ananda Herath, Minsoo Song, and John Montgomery. "ChemInform Abstract: Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition." ChemInform 43, no. 7 (2012): no. http://dx.doi.org/10.1002/chin.201207044.

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13

Hailes, Helen C., Ben Isaac та M. Hashim Javaid. "ChemInform Abstract: 1,4-Addition of Chiral 2-Propenylphosphonamide Anions to α-Substituted Cyclopentenones: Use in Enantioselective Syntheses of Methyl Dihydrojasmonates and Methyl Jasmonates." ChemInform 33, № 2 (2010): no. http://dx.doi.org/10.1002/chin.200202188.

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14

Peng, Jin-Bao, Wei-Feng Wang, and Xiao-Feng Wu. "Palladium-catalyzed carbonylative synthesis of substituted cyclopentenones from aryl iodides and internal alkynes." Organic & Biomolecular Chemistry 17, no. 24 (2019): 5882–85. http://dx.doi.org/10.1039/c9ob01019j.

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15

Chen, Sijia, Chongguo Jiang, Nan Zheng, Zhen Yang, and Lili Shi. "Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)." Catalysts 10, no. 10 (2020): 1199. http://dx.doi.org/10.3390/catal10101199.

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Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed Pauson-Khand reaction and summarizes its strategic applications in total syntheses of structurally complex natural products in the last five years. Additionally, the hetero-Pauson-Khand reaction in the synthesis of heterocycles will also be disc

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16

Conti, C., P. Mastromarino, P. Tomao, A. De Marco, F. Pica, and M. G. Santoro. "Inhibition of poliovirus replication by prostaglandins A and J in human cells." Antimicrobial Agents and Chemotherapy 40, no. 2 (1996): 367–72. http://dx.doi.org/10.1128/aac.40.2.367.

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Cyclopentenone prostaglandins (PGs) inhibit the replication of a wide variety of enveloped DNA and RNA viruses. The antiviral activity is associated with alterations in the synthesis, maturation, and intracellular translocation of viral proteins. In the present report, we describe the effects of cyclopentenone PGs PGA1 and delta 12-PGJ2 on poliovirus (PV) replication in HeLa cells. Both PGs were found to inhibit PV replication dose dependently. Virus yield was significantly reduced at nontoxic concentrations, which did not suppress RNA or protein synthesis in uninfected or PV-infected cells. B

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17

Simeonov, Svilen P., João P. M. Nunes, Krassimira Guerra, Vanya B. Kurteva, and Carlos A. M. Afonso. "Synthesis of Chiral Cyclopentenones." Chemical Reviews 116, no. 10 (2016): 5744–893. http://dx.doi.org/10.1021/cr500504w.

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18

Rinkes, I. J. "Synthese von Cyclopentenonen." Recueil des Travaux Chimiques des Pays-Bas 57, no. 2 (2010): 176–78. http://dx.doi.org/10.1002/recl.19380570207.

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19

Baumann, Marcus, and Ian Baxendale. "Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones." Synthesis 50, no. 04 (2017): 753–59. http://dx.doi.org/10.1055/s-0036-1591745.

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An efficient entry into highly substituted cyclopentanones is presented based on functionalizing cyclopentenones by means of an aza-Michael reaction with different aniline nucleophiles. The excellent diastereoselectivity of this process is ascribed to H-bonding between a tertiary alcohol and the incoming nucleophiles. Additionally, the functionalization of the parent cyclopentenones via the Baylis–Hillman reaction is demonstrated. Together, these transformations showcase the elaboration of a simple precursor by installation of versatile functionalities at either the α- or β-position of the emb

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20

Vinogradov, Maxim G., Olga V. Turova, and Sergei G. Zlotin. "Nazarov reaction: current trends and recent advances in the synthesis of natural compounds and their analogs." Org. Biomol. Chem. 15, no. 39 (2017): 8245–69. http://dx.doi.org/10.1039/c7ob01981e.

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21

Łukasik, Beata, Marian Mikołajczyk, Grzegorz Bujacz, and Remigiusz Żurawiński. "Synthesis and the absolute configuration of both enantiomers of 4,5-dihydroxy-3-(formyl)cyclopent-2-enone acetonide as a new chiral building block for prostanoid synthesis." Organic & Biomolecular Chemistry 13, no. 3 (2015): 807–16. http://dx.doi.org/10.1039/c4ob01535e.

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22

Nardi, M., P. Costanzo, A. De Nino, et al. "Water excellent solvent for the synthesis of bifunctionalized cyclopentenones from furfural." Green Chemistry 19, no. 22 (2017): 5403–11. http://dx.doi.org/10.1039/c7gc02303k.

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23

Miller, Charlotte M., Tore Benneche, and Marcus A. Tius. "First total synthesis of the marine natural products clavulolactones II and III." Organic & Biomolecular Chemistry 13, no. 13 (2015): 4051–58. http://dx.doi.org/10.1039/c5ob00074b.

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24

Żurawiński, Remigiusz, Marian Mikołajczyk, Marcin Cieślak, Karolina Królewska, and Julia Kaźmierczak-Barańska. "Synthesis and in vitro cytotoxicity of cross-conjugated prostaglandin A and J series and their hydroxy derivatives." Organic & Biomolecular Chemistry 13, no. 25 (2015): 7000–7012. http://dx.doi.org/10.1039/c5ob00550g.

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25

Ramachary, Dhevalapally B., T. Prabhakar Reddy, and A. Suresh Kumar. "Organocatalytic umpolung annulative dimerization of ynones for the synthesis of 5-alkylidene-2-cyclopentenones." Organic & Biomolecular Chemistry 15, no. 46 (2017): 9785–89. http://dx.doi.org/10.1039/c7ob02424j.

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26

Zhou, Yi, Jonathan Behrendt, Andrew J. Sutherland, and Gareth Griffiths. "Synthetic molecular mimics of naturally occurring cyclopentenones exhibit antifungal activity towards pathogenic fungi." Microbiology 157, no. 12 (2011): 3435–45. http://dx.doi.org/10.1099/mic.0.052233-0.

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The naturally occurring reactive electrophilic species 12-oxo-phytodienoic acid (12-oxo-PDA) is a potent antifungal agent, whereas the plant growth regulator jasmonic acid, which is synthesized from 12-oxo-PDA, is ineffective. To address what structural features of the molecule endow it with antifungal activity, we synthesized a series of molecular mimics of 12-oxo-PDA varying in the length of the alkyl chain at its C-4 ring position. The octyl analogue (4-octyl cyclopentenone) was the most effective at suppressing spore germination and subsequent mycelial growth of a range of fungal pathogens

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27

TAKAHASHI, Senye, Noriko ODANI, Keiichiro TOMOKIYO, et al. "Localization of a cyclopentenone prostaglandin to the endoplasmic reticulum and induction of BiP mRNA." Biochemical Journal 335, no. 1 (1998): 35–42. http://dx.doi.org/10.1042/bj3350035.

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Cyclopentenone prostaglandins (PGs) are transported into cells and stimulate the expression of various stress genes, such as that coding for BiP (an ER luminal protein). To reveal the site of action of the PGs for the induction of stress-gene expression, we introduced a fluorescent probe, pyrene, into two types of PG analogue, GIF0010 (a cyclopentenone type) and GIF0037 (a cyclopentanone type) and examined their intracellular localization in normal rat kidney cells and their ability to induce the BiP gene expression. GIF0010 accumulated around the nuclei and coincided with BiP, a resident prot

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28

Wang, Chang, Zhenzhen Gao, Leijie Zhou, et al. "Multifunctional chiral phosphine-catalyzed [3+2] annulation of Morita–Baylis–Hillman carbonates with cyclopentenones: asymmetric synthesis of 4-oxo-hexahydropentalenes." Chemical Communications 54, no. 3 (2018): 279–82. http://dx.doi.org/10.1039/c7cc08380g.

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29

Hendrickson, James B., and Paul S. Palumbo. "A new synthesis of cyclopentenones: dihydrojasmone." Journal of Organic Chemistry 50, no. 12 (1985): 2110–12. http://dx.doi.org/10.1021/jo00212a020.

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30

Ghorai, Sujit Kumar, Nirmal Kumar Hazra, and Dipakranjan Mal. "Facile Synthesis of 4‐Functionalized Cyclopentenones." Synthetic Communications 37, no. 12 (2007): 1949–56. http://dx.doi.org/10.1080/00397910701354392.

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31

Ulbrich, Kathrin, Peter Kreitmeier, Tirayut Vilaivan, and Oliver Reiser. "Enantioselective Synthesis of 4-Heterosubstituted Cyclopentenones." Journal of Organic Chemistry 78, no. 8 (2013): 4202–6. http://dx.doi.org/10.1021/jo400409f.

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32

Fiandanese, Vito, Giuseppe Marchese, Angela Punzi, and Giambattista Ruggieri. "A straightforward synthesis of substituted cyclopentenones." Tetrahedron Letters 37, no. 46 (1996): 8455–58. http://dx.doi.org/10.1016/0040-4039(96)01917-x.

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33

Serdyuk, O. V., V. T. Abaev, and A. V. Butin. "Synthesis of new cyclopentenones from phenacylfurans." Chemistry of Heterocyclic Compounds 47, no. 7 (2011): 906–8. http://dx.doi.org/10.1007/s10593-011-0852-7.

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34

Mao, Hai F., Jia C. Yuan, Ping Y. Zhang, Miao M. Jin, Ji B. Liu, and Yun Zhao. "On-line attenuated total reflection infrared spectroscopy (ATR-IR): a powerful tool for investigating the methyl cyclopentenone synthesis process." Analyst 145, no. 21 (2020): 6987–91. http://dx.doi.org/10.1039/d0an01327g.

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On-line attenuated total reflection infrared spectroscopy (ATR-IR) was used to gain a good understanding of the kinetics and mechanism for methyl cyclopentenone (MCP) synthesis from 2-methylfuran and formaldehyde in a four-step reaction.

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35

Cheng, Peter T. W., and Stewart McLean. "A total synthesis of a protected form of the secoxyloganin aglucone." Canadian Journal of Chemistry 67, no. 2 (1989): 261–67. http://dx.doi.org/10.1139/v89-043.

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A synthesis is described that leads from cyclopentadiene through 5-norbornen-2-one to the monosubstituted cyclopentenone 5; a vinyl substituent is attached by the reaction of a cuprate, and the enolate intermediate is trapped as the silyl enol ether 4, which is converted to 19, a product with the 10-carbon framework and stereochemistry of the secoxyloganin aglucone, and with all functional groups differentially protected and in the correct oxidation state. Explorations of the cuprate reaction required to convert the cyclopentenone 5 to the siloxycyclopentene 4 and of the reactions required for

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36

Trost, Barry M., Peter Seoane, Serge Mignani, and Murat Acemoglu. "Stereocontrolled cyclopentenone synthesis via cycloaddition." Journal of the American Chemical Society 111, no. 19 (1989): 7487–500. http://dx.doi.org/10.1021/ja00201a032.

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37

Ceccherelli, Paolo, Massimo Curini, Maria Carla Marcotullio, Ornelio Rosati, and Ernest Wenkert. "A new, general cyclopentenone synthesis." Journal of Organic Chemistry 55, no. 1 (1990): 311–15. http://dx.doi.org/10.1021/jo00288a052.

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38

Shen, Tao, Ruijia Hu, Chenjie Zhu, et al. "Production of cyclopentanone from furfural over Ru/C with Al11.6PO23.7 and application in the synthesis of diesel range alkanes." RSC Advances 8, no. 66 (2018): 37993–8001. http://dx.doi.org/10.1039/c8ra08757a.

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Cyclopentanone as the substrate for the synthesis of jet fuel range cyclic alkanes can be prepared through the cyclopentenone route under mild conditions and catalyzed by Ru/C with Al<sub>11.6</sub>PO<sub>23.7</sub> from furfural.

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39

Teimouri, Mohammad Bagher, Mahdi Heydari, and Kazem Mohammadi. "Substrate-controlled selectivity switch in a three-component reaction: sequential synthesis of spiro-oxazolidinedione-cyclopentenones and hydroxy enaminobarbiturates in water." RSC Advances 10, no. 23 (2020): 13601–10. http://dx.doi.org/10.1039/d0ra01699c.

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40

Egorov, Victor A., Fanuza A. Gimalova, Gullira M. Khalikova, and Mansur S. Miftakhov. "Design and synthesis of novel polyheterofunctionalyzed cyclopentenones." Tetrahedron 68, no. 35 (2012): 7122–28. http://dx.doi.org/10.1016/j.tet.2012.06.048.

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41

Stathakis, Christos I., and John K. Gallos. "Traceless solid-phase synthesis of hydroxylated cyclopentenones." Tetrahedron Letters 49, no. 48 (2008): 6804–6. http://dx.doi.org/10.1016/j.tetlet.2008.09.080.

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42

Matsuyama, Haruo, Yasuyuki Miyazawa, Yuji Takei, and Michio Kobayashi. "Regioselective synthesis of cyclopentenones from 4-thianone." Journal of Organic Chemistry 52, no. 9 (1987): 1703–10. http://dx.doi.org/10.1021/jo00385a011.

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43

Varea, Teresa, Ana Alcalde, Carolina López de Dicastillo, Carmen Ramírez de Arellano, Fernando P. Cossío, and Gregorio Asensio. "Selective “One-Pot” Synthesis of Functionalized Cyclopentenones." Journal of Organic Chemistry 77, no. 14 (2012): 6327–31. http://dx.doi.org/10.1021/jo300806y.

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44

Liu, Peng, and Chung K. Chu. "Enantiomeric synthesis of carbocyclic analogs of D- and L-6-azapyrimidine ribonucleosides." Canadian Journal of Chemistry 84, no. 4 (2006): 748–54. http://dx.doi.org/10.1139/v06-052.

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An effective and practical synthesis of carbocyclic D- and L-6-azapyrimidine nucleosides (38) was described. Starting from D-ribose, a new efficient methodology for the synthesis of L-2,3-O-cyclohexylidene-4-cyclopentenone (23) was developed via a ring-closing metathesis, which was applied for the synthesis of L-cyclopentyl-6-azapyrimidine nucleosides (68). The regiospecific introduction of 6-azauracil on the carbocyclic moiety (9 and 25) was also achieved by masking its N3 position with a 4-methylthio group.Key words: carbocyclic nucleosides, 6-azapyrimidine nucleosides, enantiomeric synthe

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45

TAKANO, SEIICHI, YOSHIHARU IWABUCHI, MICHIYASU TAKAHASHI, and KUNIO OGASAWARA. "A convenient synthesis of 2-cyclopentenone." CHEMICAL & PHARMACEUTICAL BULLETIN 34, no. 8 (1986): 3445–46. http://dx.doi.org/10.1248/cpb.34.3445.

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46

Trost, Barry M., and Anthony B. Pinkerton. "A New Strategy for Cyclopentenone Synthesis." Organic Letters 2, no. 11 (2000): 1601–3. http://dx.doi.org/10.1021/ol005853a.

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47

Pashkovsky, F. S., Yu S. Dontsu, D. I. Korneev, D. B. Rubinov та F. A. Lakhvich. "One-pot synthesis of cyclic β-dicarbonyl compounds as synthons for 11-deoxyprostanoids". Doklady of the National Academy of Sciences of Belarus 64, № 2 (2020): 186–92. http://dx.doi.org/10.29235/1561-8323-2020-64-2-186-192.

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One-pot synthesis of cyclic β-dicarbonyl synthons for 11-deoxyprostanoids has been developed on the basis of cyclopentane-1,3-dione and 5-phenyl tetronic acid. The obtained 2-alkyl(arylalkyl)-substituted cyclopentane-1,3-diones have been transformed into cyclopentenone precursors of 11-deoxy-PGE 1 and 11-deoxy-PGE 2 analogues.

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48

Sakagami, Yukari, Naoki Kondo, Yuki Sawayama, Hiroyuki Yamakoshi, and Seiichi Nakamura. "Total Syntheses of Marrubiin and Related Labdane Diterpene Lactones." Molecules 25, no. 7 (2020): 1610. http://dx.doi.org/10.3390/molecules25071610.

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Total syntheses of the labdane diterpene lactones marrubiin, marrulibacetal, desertine, marrulibacetal A, marrubasch F, cyllenine C, marrulanic acid, and marrulactone are described. The trans-decalin moiety of these molecules was constructed in a stereoselective manner by a Pauson-Khand reaction, and the resultant cyclopentenone was oxidatively cleaved for formation of the lactone ring. Elongation of the side chain at C9 was achieved by an epoxide-opening reaction with a variety of nucleophiles, and the functional group manipulations completed the syntheses of these natural products. Stereoche

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49

Shimizu, Ken-ichi, Mina Tomita, Ken-ichi Fuhshuku, Takeshi Sugai, and Mitsuru Shoji. "Formal Synthesis of (+)-Madindoline A a Potent IL-6 Inhibitor Utilizing Enzymatic Discrimination of Quaternary Carbon." Natural Product Communications 8, no. 7 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800710.

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A formal synthesis of (+)-madindoline A was achieved. The Sunazuka's key intermediate (4 R,5 S)-(–)-3-butyl-4-( tert-butyldimethylsiloxy)-5-methoxycarbonyl-2,5-dimethyl-2-cyclopentenone was synthesized from easily available (2 S,3 S)-3-acetoxy-2-ethenyl-2-methylcyclopentanone. The starting material was reliably supplied by a chemo-enzymatic procedure in enantiomerically pure form. The synthesis was performed by straightforward transformations involving enone formation and regioselective introduction of the two alkyl side chains.

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50

Holland, Herbert L., Elaref S. Ratemi, and Luis Contreras. "Synthesis of (±)-15-thia-15-deoxy-PGE1 methyl ester." Canadian Journal of Chemistry 72, no. 1 (1994): 1–5. http://dx.doi.org/10.1139/v94-001.

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The 15-thia-15-deoxy analogue of prostaglandin E1 methyl ester has been prepared by the zirconocene chloride mediated conjugate addition of an n-pentyl ethynyl sulfide derived anion to an appropriately substituted cyclopentenone. Similar methodology has also been used to prepare other 3-(3′-thia-1′-octenyl)-cyclopentanones.

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