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Journal articles on the topic 'Bicyclic lactones'

Author: Grafiati

Published: 4 June 2021

Last updated: 4 February 2022

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1

Chany, Anne-Caroline, Léo B. Marx, and Jonathan W. Burton. "Synthesis of bicyclic tetrahydrofurans from linear precursors using manganese(iii) acetate." Organic & Biomolecular Chemistry 13, no. 35 (2015): 9190–93. http://dx.doi.org/10.1039/c5ob01091h.

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Cyclisation of a range of alkoxy-malonates in the presence of manganese(iii) acetate gives rise to bicyclic lactone/THFs and lactone/lactones in synthetically useful yields and diastereoselectivities.

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2

Deslongchamps, Pierre, Daniel Guay, and Robert Chènevert. "The hydrolysis of cis and trans methoxy bicyclic and tricyclic orthoesters. Evidence for a chair–boat inversion prior to breakdown in some hemiorthoester tetrahedral intermediates." Canadian Journal of Chemistry 63, no. 9 (1985): 2493–500. http://dx.doi.org/10.1139/v85-413.

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The acid hydrolysis of cis and trans methoxy bicyclic and tricyclic orthoesters 1–4 was studied. The trans isomers gave only the corresponding hydroxy-lactones (2 → 14 and 4 → 16 + 10) whereas the cis isomers gave mixtures of dihydroxy-esters and hydroxy-lactones (1 → 13 + 14) and 3 → 15 + 16 + 10). These results are rationalized on the basis of the stereoelectronic theory for hydrolytic processes. The fact that hydroxy-lactone 16 is produced to a larger extent than the isomeric hydroxy-lactone 10 is taken as evidence that when a tetrahedral intermediate is not allowed (stereoelectronically) t

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3

Markó, I., and N. Maulide. "Stereoselective Synthesis of Bicyclic Lactones from Furans." Synfacts 2006, no. 5 (2006): 0429. http://dx.doi.org/10.1055/s-2006-934372.

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4

Finta, Zoltán, Zoltán Hell, Agnieszka Cwik, and László Tőke. "A Simple Synthesis of 1,1,2-tris-(Hydroxymethyl)-Cyclopropane and Its Dihalo Derivatives." Journal of Chemical Research 2002, no. 9 (2002): 459–60. http://dx.doi.org/10.3184/030823402103172653.

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The phase transfer catalytic cyclopropanation of the malonic ester of allylic alcohol or its 3,3-dibromo and 3,3-dichloro derivatives yields bicyclic cyclopropane carboxylic acid lactones; reduction of these lactones with LiAlH4 in boiling THF yields the appropriate 1,1,2-tris-(hydroxymethyl)cyclopropanes in satisfactory yield.

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5

Kowalczyk, Dorota, та Łukasz Albrecht. "An organocatalytic cis-selective approach to bicyclic δ-lactones". Organic & Biomolecular Chemistry 15, № 35 (2017): 7286–89. http://dx.doi.org/10.1039/c7ob01570d.

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6

Liu, Rai-Shung. "Synthesis of oxygen heterocycles via alkynyltungsten compounds." Pure and Applied Chemistry 73, no. 2 (2001): 265–69. http://dx.doi.org/10.1351/pac200173020265.

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This short review article covers some useful applications of alkynyltungsten compounds to the syntheses of complex lactones. Two types of cyclizations will be emphasized: (1) cycloalkenylation of tungsten-alkynol compounds with aldehydes to give a-alkylidene oxacarbeniums, further leading to a-alkylidene lactones and (2) intramolecular [3+2]-cycloaddition of epoxides to give bicyclic lactones. The new methodologies can provide a short synthesis of enantiopure lactones such as (-) -epilitsenolide C2, (+) -listenolide C1, (+) -isodihydromahubanolide A, (+) -blastmycinone, and (-) -epi-blastmycin

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7

Yin, Xianglin, Haroon Mohammad, Hassan E. Eldesouky, Ahmed Abdelkhalek, Mohamed N. Seleem, and Mingji Dai. "Rapid synthesis of bicyclic lactones via palladium-catalyzed aminocarbonylative lactonizations." Chemical Communications 53, no. 53 (2017): 7238–41. http://dx.doi.org/10.1039/c7cc02494k.

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8

Y. Makama, Bello. "Stereoselective Synthesis of Bicyclic Lactones Via Annelation Protocol." American Journal of Organic Chemistry 2, no. 6 (2012): 127–31. http://dx.doi.org/10.5923/j.ajoc.20120206.01.

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9

Moloney, Mark, Plamen Angelov, Kallappa Hosamani, Yong-chul Jeong, Amber Thompson, and Muhammad Yaqoob. "Synthesis and Antibacterial Activity of Bicyclic Lactam-Lactones." Synlett 2011, no. 15 (2011): 2181–84. http://dx.doi.org/10.1055/s-0030-1261197.

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10

Wongsa, N., K. Kanokmedhakul, J. Boonmak, S. Youngme, and S. Kanokmedhakul. "Bicyclic lactones and racemic mixtures of dimeric styrylpyrones from the leaves of Miliusa velutina." RSC Advances 7, no. 41 (2017): 25285–97. http://dx.doi.org/10.1039/c7ra01609c.

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11

Gładkowski, Witold, Małgorzata Grabarczyk, Monika Konopka та Czesław Wawrzeñczyk. "Lactones 20 : Biohydroxylation of saturated bicyclic γ-lactones with the substituted cyclohexane system". Journal of Molecular Catalysis B: Enzymatic 29, № 1-6 (2004): 13–18. http://dx.doi.org/10.1016/j.molcatb.2003.10.012.

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12

Grabarczyk, Małgorzata, Wanda Mączka, Katarzyna Wińska, et al. "Pleurotus ostreatus as a Biocatalyst to Obtain Bicyclic Hydroxylactones with Three or Four Methyl Groups." Catalysts 9, no. 8 (2019): 643. http://dx.doi.org/10.3390/catal9080643.

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The purpose of the study was to explore microbial transformations in cultures of basidiomycetes Pleurotus ostreatus, two bicyclic unsaturated lactones occurring in the form of two diastereoisomers. Some of these strains were able to transform unsaturated lactones into four known and three new derivatives. The structures of all lactones were established on the basis of spectroscopic data. Both substrates and products caused a complete inhibition of growth of A. alternata and F. linii strains.

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13

Wińska, Katarzyna, Małgorzata Grabarczyk, Wanda Mączka, Barbara Żarowska, Gabriela Maciejewska, and Mirosław Anioł. "Influence of structure of lactones with the methylcyclohexene and dimethylcyclohexene ring on their biotransformation and antimicrobial activity." Zeitschrift für Naturforschung C 72, no. 5-6 (2017): 209–17. http://dx.doi.org/10.1515/znc-2016-0188.

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Abstract The aim of this article is influence of the structure of lactones with the methylcyclohexene and dimethylcyclohexene ring on their biotransformation and antimicrobial activity. This work was based on the general remark that even the smallest change in the structure of a compound can affect its biological properties. The results of the biotransformation of four bicyclic unsaturated lactones with one or two methyl groups in the cyclohexene ring was tested using fifteen fungal strains (Fusarium species, Penicillium species, Absidia species, Cunninghamella japonica, and Pleurotus ostreatu

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14

Abbasov, Mikail E., Brandi M. Hudson, Dean J. Tantillo та Daniel Romo. "Stereodivergent, Diels–Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application". Chemical Science 8, № 2 (2017): 1511–24. http://dx.doi.org/10.1039/c6sc04273b.

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15

Subba Reddy, B. V., Dhanraj O. Biradar, Y. Vikram Reddy, J. S. Yadav, Kiran Kumar Singarapu, and B. Sridhar. "Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A." Organic & Biomolecular Chemistry 14, no. 37 (2016): 8832–37. http://dx.doi.org/10.1039/c6ob01686c.

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16

Dams, Iwona, Agata Białońska, Zbigniew Ciunik, and Czesław Wawrzeńczyk. "Lactones 23: Synthesis of cis-fused bicyclic hydroxy lactones with a p-menthane system." Tetrahedron: Asymmetry 16, no. 12 (2005): 2087–97. http://dx.doi.org/10.1016/j.tetasy.2005.04.020.

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17

Oliveira, Renata B. de, Ricardo J. Alves, José Dias de Souza Filho, and Maria Auxiliadora F. Prado. "Stereoselective synthesis of carbohydrate-based fused bicyclic delta-lactones." Journal of the Brazilian Chemical Society 14, no. 3 (2003): 442–48. http://dx.doi.org/10.1590/s0103-50532003000300017.

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18

Ahmad, Zafeer, Uttam Kumar Ray, and R. V. Venkateswaran. "Synthesis of hexahydrobenzopyranones : bicyclic precursor lactones to the trichothecenes." Tetrahedron 46, no. 3 (1990): 957–66. http://dx.doi.org/10.1016/s0040-4020(01)81375-2.

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19

Listkowski, Arkadiusz, Otman Otman, Stéphane Chambert, and Yves Queneau. "Synthesis and use of new C-glycosyl bicyclic lactones." Tetrahedron Letters 56, no. 35 (2015): 5051–53. http://dx.doi.org/10.1016/j.tetlet.2015.07.017.

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20

Sengupta, Dipanjan, Arun Ghosh, and R. V. Venkateswaran. "Convenient Synthesis of Bicyclic Lactones Related to the Trichothecenes." Synthetic Communications 18, no. 18 (1988): 2303–8. http://dx.doi.org/10.1080/00397918808082374.

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21

Jiang, Zhi-Hong, Qing-Xiong Yang, Takashi Tanaka, and Isao Kouno. "Bicyclic Polyketide Lactones from Chinese Medicinal Ants,Polyrhacis lamellidens." Journal of Natural Products 71, no. 4 (2008): 724–27. http://dx.doi.org/10.1021/np070558l.

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22

Roux, Marie-Claude, Lya Wartski, Martine Nierlich, Daniel Vigner, and Monique Lance. "Easy access to highly functionalized bicyclic lactones and ketones." Tetrahedron 50, no. 28 (1994): 8445–56. http://dx.doi.org/10.1016/s0040-4020(01)85565-4.

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23

Veedu, Rakesh N., David Kvaskoff, and Curt Wentrup. "Sydnone Photochemistry: Direct Observation of Earl's Bicyclic Lactone Valence Isomers (Oxadiazabicyclo[2.1.0]pentanones), Formation of Carbodiimides, Reaction Mechanism, and Photochromism." Australian Journal of Chemistry 67, no. 3 (2014): 457. http://dx.doi.org/10.1071/ch13536.

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The matrix photolyses of 3-phenyl-, 3-pyridyl, and 3,4-diphenylsydnones 16, 19, and 22 were investigated by matrix-isolation infrared spectroscopy. The formation of the neutral, bicyclic lactone valence isomers postulated by Earl – the oxadiazabicyclo[2.1.0]pentanones exo-17 and exo-20 – was clearly observed in the first two cases and is also likely in the case of exo-23 (C=O absorptions in the IR at 1881, 1886, and 1874 cm–1, respectively). The efficient photodecomposition of sydnones to carbodiimides RN=C=NR′ (18, 21, and 24) and CO2 was established in all three cases. The formation of benzo

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24

Gładkowski, Witold, Małgorzata Grabarczyk, Katarzyna Wińska та ін. "Lactones 26 : Stereoselective microbial epoxidation of unsaturated bicyclic γ-lactones with the alkylsubstituted cyclohexane system". Journal of Molecular Catalysis B: Enzymatic 49, № 1-4 (2007): 79–87. http://dx.doi.org/10.1016/j.molcatb.2007.08.006.

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25

Horwitz, Matthew A., Elisabetta Massolo, and Jeffrey S. Johnson. "Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition." Beilstein Journal of Organic Chemistry 13 (April 24, 2017): 762–67. http://dx.doi.org/10.3762/bjoc.13.75.

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We report a desymmetrization of cyclohexadienones by intramolecular conjugate addition of a tethered dithiane nucleophile. Mild reaction conditions allow the formation of diversely functionalized fused bicyclic lactones. The products participate in facially selective additions from the convex surface, leading to allylic alcohol derivatives.

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26

Brandvold, Timothy A., William D. Wulff, and Arnold L. Rheingold. "Efficient entry to bicyclic lactones via van Halban-White cyclizations." Journal of the American Chemical Society 112, no. 4 (1990): 1645–47. http://dx.doi.org/10.1021/ja00160a063.

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27

Guibé-Jampel, E., G. Rousseau, and L. Blanco. "Enzymatic resolution of racemic bicyclic lactones by horse liver esterase." Tetrahedron Letters 30, no. 1 (1989): 67–68. http://dx.doi.org/10.1016/s0040-4039(01)80324-5.

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28

Ferraz, Helena M. C., та Luiz S. Longo. "Bicyclic β-Hydroxytetrahydrofurans as Precursors of Medium Ring Keto-Lactones". Journal of Organic Chemistry 72, № 8 (2007): 2945–50. http://dx.doi.org/10.1021/jo0626109.

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29

Liang, Kwei-Wen, Malapaka Chandrasekharam, Chien-Le Li, and Rai-Shung Liu. "Efficient Synthesis of Bicyclic Lactones via Tungsten-Mediated Intramolecular Cycloalkenation." Journal of Organic Chemistry 63, no. 21 (1998): 7289–93. http://dx.doi.org/10.1021/jo980728m.

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30

Hell, Z. "Diastereoselectivity in the formation of bicyclic cyclopropane carboxylic acid lactones." Tetrahedron 55, no. 5 (1999): 1367–76. http://dx.doi.org/10.1016/s0040-4020(98)01109-0.

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31

Wu, Xuesong, Zhiwei Chen, Yu-Bin Bai та Vy M. Dong. "Diastereodivergent Construction of Bicyclic γ-Lactones via Enantioselective Ketone Hydroacylation". Journal of the American Chemical Society 138, № 37 (2016): 12013–16. http://dx.doi.org/10.1021/jacs.6b06227.

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32

Cai, Xinpei, Weida Liang, Mingxin Liu, Xiating Li, and Mingji Dai. "Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones." Journal of the American Chemical Society 142, no. 32 (2020): 13677–82. http://dx.doi.org/10.1021/jacs.0c06179.

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33

Maulide, Nuno, and István E. Markó. "Stereoselective synthesis of bicyclic lactones by annelation with functionalised orthoesters." Chemical Communications, no. 11 (2006): 1200. http://dx.doi.org/10.1039/b600677a.

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34

Burton, Jonathan W., Paul T. O’Sullivan, Edward A. Anderson, Andrew B. Holmes, and Ian Collins. "Synthesis of fused bicyclic medium-ring lactones via Claisen rearrangement." Chemical Communications, no. 7 (2000): 631–32. http://dx.doi.org/10.1039/b000303o.

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35

Hui, Andrew, Antony J. Fairbanks, Robert J. Nash та ін. "Aldol equilibrations of unprotected trihydroxybicyclic lactones: Enantiomeric tetrahydroxy-α-aminocyclopentane carboxylic acids from epimeric bicyclic lactones". Tetrahedron Letters 35, № 47 (1994): 8895–98. http://dx.doi.org/10.1016/s0040-4039(00)78528-5.

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36

Lu, Wen-Qiang, Dian-Bing Zhou, Zheng-Chun Yin, Qing-Song Liu, and Guan-Wu Wang. "A copper-promoted synthesis of epoxy-bridged [60]fullerene-fused lactones and further derivatization." Chemical Communications 57, no. 57 (2021): 7043–46. http://dx.doi.org/10.1039/d1cc02669k.

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The copper-promoted decarboxylative annulation of C<sub>60</sub> with two identical α-oxocarboxylic acids affords the unique epoxy-bridged C<sub>60</sub>-fused lactones, which can be further transformed into epoxy-bridged C<sub>60</sub>-fused hemiacetals and bicyclic-fused 1,2,3,4-adducts.

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37

Lewis, Jason G., and Paul A. Bartlett. "Amino Acid-Derived Heterocycles as Combinatorial Library Targets: Bicyclic Aminal Lactones." Journal of Combinatorial Chemistry 5, no. 3 (2003): 278–84. http://dx.doi.org/10.1021/cc020082i.

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38

ROUX, M. C., L. WARTSKI, M. NIERLICH, D. VIGNER, and M. LANCE. "ChemInform Abstract: Easy Access to Highly Functionalized Bicyclic Lactones and Ketones." ChemInform 25, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199449076.

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39

Hanessian, S., Y. L. Bennani, and R. Di Fabio. "Intramolecular free-radical ring closures. II. Structures of two bicyclic lactones." Acta Crystallographica Section C Crystal Structure Communications 46, no. 5 (1990): 937–39. http://dx.doi.org/10.1107/s0108270189010784.

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40

Ferreira, J. Tércio B., Ronaldo C. Boscaini, Francisco A. Marques, and J. Zukerman-schpector. "Synthesis of A Bicyclic Lactone, Structurally Modelled On an Early Structure Assignment of the Otoba Parvifolia Lactones." Natural Product Letters 1, no. 4 (1993): 305–10. http://dx.doi.org/10.1080/10575639308050065.

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41

Mazur, Marcelina, Witold Gładkowski, Aleksandra Pawlak, Bożena Obmińska-Mrukowicz, Gabriela Maciejewska та Czesław Wawrzeńczyk. "Microbial Asymmetric Functionalization of β-Cyclocitral-Derived Tetramethyl-Substituted γ-Lactone". Molecules 24, № 4 (2019): 666. http://dx.doi.org/10.3390/molecules24040666.

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Searching for the new anticancer compounds we prepared three new β-cyclocitral-derived hydroxyl-γ-lactones by microbial hydroxylation of tetramethyl-substituted bicyclic γ-lactone. The substrate was transformed by the enzymatic system of filamentous fungi. Three out of fifteen strains were selected as effective biocatalysts (Fusarium culmorum AM10, Armillaria mellea AM296, Trametes versicolor AM536). The hydroxylation processes were not only regioselective but also stereoselective. The hydroxylation products of each secondary carbon atom in the cyclohexane ring were obtained by the application

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42

HUI, A., A. J. FAIRBANKS, R. J. NASH та ін. "ChemInform Abstract: Aldol Equilibrations of Unprotected Trihydroxybicyclic Lactones: Enantiomeric Tetrahydroxy-α-Aminocyclopentane Carboxylic Acids from Epimeric Bicyclic Lactones." ChemInform 26, № 16 (1995): no. http://dx.doi.org/10.1002/chin.199516245.

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43

Sut, Stefania, Filippo Maggi, Marcello Nicoletti, Valeria Baldan, and Stefano Dall`Acqua. "New Drugs from Old Natural Compounds: Scarcely Investigated Sesquiterpenes as New Possible Therapeutic Agents." Current Medicinal Chemistry 25, no. 10 (2018): 1241–58. http://dx.doi.org/10.2174/0929867324666170404150351.

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Sesquiterpenes are natural products that have been extensively studied for their bioactivities, evidencing their potentiality as useful scaffolds for the development of drugs. Considering the different derivatives, the sesquiterpene lactones have been evaluated, especially on cancer cell and antineoplastic efficacy in in vivo studies. Their bioactivity is strictly related to the presence of the reactive α-methylene-γ-lactone group (αMγL). Nevertheless, several other sesquiterpenes lacking αMγL are known and have been studied for their biological effects and potential usefulness in the developm

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44

Hanessian, Stephen, and Kiran Kumar Kothakonda. "Design and synthesis of oxazolidinone ketolide antibiotic segment mimetics." Canadian Journal of Chemistry 83, no. 6-7 (2005): 801–11. http://dx.doi.org/10.1139/v05-095.

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Macrolides have been modified to a large extent by structural and functional variants to expand their spectrum of activity and overcome resistance. Ketolides are new generation 14-membered ring macrolides derived by chemical modification of the readily available erythromycin A. We have designed and synthesized bicyclic oxazolidinone-δ-lactones to mimic the "left segment" periphery of ketolides.Key words: macrolide, ketolide, 50S r-RNA, segment mimetics.

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45

Roux, Marie-Claude, Lya Wartski, Martine Nierlich та Monique Lance. "Enantioselective synthesis of unsubstituted and 3-substituted-4-aroyl-δ-lactones. Easy way to enantiopure bicyclic lactone systems". Tetrahedron 52, № 30 (1996): 10083–94. http://dx.doi.org/10.1016/0040-4020(96)00542-x.

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46

Yin, Jian, and Torsten Linker. "Stereoselective diversity-oriented syntheses of functionalized saccharides from bicyclic carbohydrate 1,2-lactones." Tetrahedron 67, no. 13 (2011): 2447–61. http://dx.doi.org/10.1016/j.tet.2011.01.069.

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47

Bøjstrup, Marie, Mette Fanefjord, and Inge Lundt. "Aminocyclopentanols as sugar mimics. Synthesis from unsaturated bicyclic lactones by Overman rearrangement." Organic & Biomolecular Chemistry 5, no. 19 (2007): 3164. http://dx.doi.org/10.1039/b710232a.

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48

Fuchs, Sébastien, Valérie Berl, and Jean-Pierre Lepoittevin. "A Highly Stereoselective Divergent Synthesis of Bicyclic Models of Photoreactive Sesquiterpene Lactones." European Journal of Organic Chemistry 2007, no. 7 (2007): 1145–52. http://dx.doi.org/10.1002/ejoc.200600611.

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49

Hell, Zoltan, Zoltan Finta, Tamas Gruenvald, et al. "ChemInform Abstract: Diastereoselectivity in the Formation of Bicyclic Cyclopropane Carboxylic Acid Lactones." ChemInform 30, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199925093.

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50

Burton, Jonathan W., Paul T. O'Sullivan, Edward A. Anderson, Ian Collins, and Andrew B. Holmes. "ChemInform Abstract: Synthesis of Fused Bicyclic Medium-Ring Lactones via Claisen Rearrangement." ChemInform 31, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.200031179.

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