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Journal articles on the topic 'Δ-Lactams'

Author: Grafiati

Published: 25 January 2025

Last updated: 31 July 2025

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1

Coullon, Héloise, Aline Rifflet, Richard Wheeler, Claire Janoir, Ivo Gomperts Boneca та Thomas Candela. "N-Deacetylases required for muramic-δ-lactam production are involved in Clostridium difficile sporulation, germination, and heat resistance". Journal of Biological Chemistry 293, № 47 (2018): 18040–54. http://dx.doi.org/10.1074/jbc.ra118.004273.

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Spores are produced by many organisms as a survival mechanism activated in response to several environmental stresses. Bacterial spores are multilayered structures, one of which is a peptidoglycan layer called the cortex, containing muramic-δ-lactams that are synthesized by at least two bacterial enzymes, the muramoyl-l-alanine amidase CwlD and the N-deacetylase PdaA. This study focused on the spore cortex of Clostridium difficile, a Gram-positive, toxin-producing anaerobic bacterial pathogen that can colonize the human intestinal tract and is a leading cause of antibiotic-associated diarrhea.

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2

Glover, Stephen A., Adam A. Rosser, Avat (Arman) Taherpour, and Ben W. Greatrex. "Formation and HERON Reactivity of Cyclic N,N-Dialkoxyamides." Australian Journal of Chemistry 67, no. 3 (2014): 507. http://dx.doi.org/10.1071/ch13557.

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Cyclic N,N-dialkoxyamides have been made, for the first time, by hypervalent iodine oxidation of β- and γ-hydroxyhydroxamic esters 17, 19, and 21. The fused γ-lactam products, N-butoxy- and N-benzyloxybenzisoxazolones (22a and 22b), are stable while alicyclic γ-lactam and δ-lactam products, 24 and 25, although observable by NMR spectroscopy and ESI-MS are unstable at room temperature, undergoing HERON reactions. The γ-lactam 24 undergoes exclusive ring opening to give a butyl ester-functionalised alkoxynitrene 28. The δ-lactam 25, instead, undergoes a HERON ring contraction to give butyrolacto

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3

Wang, Xin, Jia Lei, Guofeng Li, et al. "Synthetic methods for compounds containing fluoro-lactam units." Organic & Biomolecular Chemistry 18, no. 48 (2020): 9762–74. http://dx.doi.org/10.1039/d0ob02168g.

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This review highlights recent progress in the construction of fluorinated lactams, including fluoro-β-lactams, fluoro-γ-lactams, and fluoro-δ-lactams, with an emphasis on the scopes, limitations and mechanisms of these different reactions.

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4

Boudreault, Nicolas, Richard G. Ball, Christopher Bayly, Michael A. Bernstein та Yves Leblanc. "Conformational analysis of δ-lactams". Tetrahedron 50, № 27 (1994): 7947–56. http://dx.doi.org/10.1016/s0040-4020(01)85279-0.

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5

Domingo, Luis R., та José A. Sáez. "Understanding the selectivity in the formation of δ-lactams vs. β-lactams in the Staudinger reactions of chloro-cyan-ketene with unsaturated imines. A DFT study". RSC Adv. 4, № 102 (2014): 58559–66. http://dx.doi.org/10.1039/c4ra10291f.

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6

Rossi-Ashton, James A., Richard J. K. Taylor, and William P. Unsworth. "Selective synthesis of three product classes from imine and carboxylic acid precursors via direct imine acylation." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7527–32. http://dx.doi.org/10.1039/c7ob02039b.

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7

Diaba, Faïza, Alexandra G. Sandor та María del Carmen Morán. "Microwave-Assisted Atom Transfer Radical Cyclization in the Synthesis of 3,3-Dichloro-γ- and δ-Lactams from N-Alkenyl-Tethered Trichloroacetamides Catalyzed by RuCl2(PPh3)3 and Their Cytotoxic Evaluation". Molecules 29, № 9 (2024): 2035. http://dx.doi.org/10.3390/molecules29092035.

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An expeditious synthesis of γ- and δ-lactams from tethered alkenyl trichloroacetamides in the presence of 5% of RuCl2(PPh3)3 is reported. In this investigation we have demonstrated that microwave activation significantly enhances reaction rates, leading to the formation of the corresponding lactams in yields ranging from good to excellent. Thus, we have been able to prepare a wide range of lactams, including indole and morphan bicyclic scaffolds, where the corresponding reactions were completely diastereoselective. This process was successfully extended to α,α-dichloroamides without affecting

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8

Albrecht, Anna, Łukasz Albrecht та Tomasz Janecki. "Recent Advances in the Synthesis of α-Alkylidene-Substituted δ-Lactones, γ-Lactams and δ-Lactams". European Journal of Organic Chemistry 2011, № 15 (2011): 2747–66. http://dx.doi.org/10.1002/ejoc.201001486.

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9

Fleet, George W. J., Nigel G. Ramsden, Raymond A. Dwek та ін. "δ-Lactams: synthesis fromD-glucose, and preliminiary evaluation as a fucosidase inhibitor, ofL-fuconic-δ-lactam". J. Chem. Soc., Chem. Commun., № 7 (1988): 483–85. http://dx.doi.org/10.1039/c39880000483.

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10

Gan, Miaomiao, Lan Jiang та Zhengning Li. "Diastereoselective Synthesis of γ-Lactams and δ-Lactams via a Conjugate Addition-Initiated Tandem Reaction". Synlett 30, № 12 (2019): 1447–51. http://dx.doi.org/10.1055/s-0037-1611552.

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β-Alkoxycarbonyl-γ-lactams and γ-alkoxycarbonyl-δ-lactams were synthesized via a conjugate alkylation/Mannich reaction/lactamization tandem reaction of unsaturated dicarboxylates with diethyl zinc and aldimines. The high yield, the ready availability of the reagents, and especially the high diastereoselectivity are promising characteristics of the approach that allows access to functionalized lactams.

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11

Cogswell, Thomas J., Craig S. Donald, De-Liang Long та Rodolfo Marquez. "Short and efficient synthesis of fluorinated δ-lactams". Organic & Biomolecular Chemistry 13, № 3 (2015): 717–28. http://dx.doi.org/10.1039/c4ob01547a.

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12

Jarvis, Claire L., Neyra M. Jemal, Spencer Knapp, and Daniel Seidel. "Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins." Organic & Biomolecular Chemistry 16, no. 23 (2018): 4231–35. http://dx.doi.org/10.1039/c8ob01015c.

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13

Albrecht, Anna, Lukasz Albrecht та Tomasz Janecki. "ChemInform Abstract: Recent Advances in the Synthesis of α-Alkylidene-Substituted δ-Lactones, γ-Lactams and δ-Lactams". ChemInform 42, № 41 (2011): no. http://dx.doi.org/10.1002/chin.201141234.

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14

Gnilka, Radoslaw, та Czeslaw Wawrzeńczyk. "Synthesis of Sabina δ-Lactones and Sabina δ-Lactams from (+)-Sabinene". Australian Journal of Chemistry 66, № 11 (2013): 1399. http://dx.doi.org/10.1071/ch13306.

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Two sabina δ-lactones (3 and 4) were obtained in a two-step synthesis from (+)-sabinene (1). The oxidation of (+)-sabinene (1) with potassium permanganate and sodium periodate to (–)-sabina ketone (2) was the first step. In the second step, the ketone obtained was subjected to chemical and microbial Baeyer–Villiger oxidation. Chemical Baeyer–Villiger oxidation of this ketone afforded two δ-lactones 3 and 4 whereas microbial Baeyer–Villiger oxidation afforded only ‘abnormal’ δ-lactone 4. (–)-Sabina ketone was also the starting material for the synthesis of new δ-lactams (7 and 8). They were obt

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15

Albrecht, Łukasz, Bo Richter, Henryk Krawczyk та Karl Anker Jørgensen. "Enantioselective Organocatalytic Approach to α-Methylene-δ-lactones and δ-Lactams". Journal of Organic Chemistry 73, № 21 (2008): 8337–43. http://dx.doi.org/10.1021/jo801582t.

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16

Schmidt, Johannes Philipp, та Bernhard Breit. "Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G". Chemical Science 10, № 10 (2019): 3074–79. http://dx.doi.org/10.1039/c8sc05502e.

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17

Boltjes, André, George P. Liao, Ting Zhao, Eberhardt Herdtweck та Alexander Dömling. "Ugi 4-CR synthesis of γ- and δ-lactams providing new access to diverse enzyme interactions, a PDB analysis". Med. Chem. Commun. 5, № 7 (2014): 949–52. http://dx.doi.org/10.1039/c4md00162a.

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18

He, Chonglong, Yipeng Zhou, Zhanhuan Li, Jianfeng Xu та Xingkuan Chen. "N-Heterocyclic carbene catalyzed asymmetric [3 + 3] cycloaddtion of β,β-disubstituted, α,β-unsaturated carboxylic esters with 3-aminobenzofurans". Organic Chemistry Frontiers 8, № 7 (2021): 1569–74. http://dx.doi.org/10.1039/d0qo01489c.

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19

Alves, Nuno G., Américo J. S. Alves, Maria I. L. Soares та Teresa M. V. D. Pinho e Melo. "Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams". Advanced Synthesis & Catalysis 363, № 10 (2021): 2464–501. http://dx.doi.org/10.1002/adsc.202100013.

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20

Zhang, Zhi-Qiang, and Feng Liu. "CuX2-mediated oxybromination/aminochlorination of unsaturated amides: synthesis of iminolactones and lactams." Organic & Biomolecular Chemistry 13, no. 24 (2015): 6690–93. http://dx.doi.org/10.1039/c5ob00520e.

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21

Diaba, Faïza, Enrique Gómez-Bengoa, Juan M. Cuerva, Josep Bonjoch та José Justicia. "Synthesis of substituted γ- and δ-lactams based on titanocene(iii)-catalysed radical cyclisations of trichloroacetamides". RSC Advances 6, № 60 (2016): 55360–65. http://dx.doi.org/10.1039/c6ra12180b.

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22

Sun, Baomin, Lijiu Gao, Shide Shen та ін. "NHC-catalyzed [4 + 2] annulation of 2-bromo-2-enals with acylhydrazones: enantioselective synthesis of δ-lactams". Organic & Biomolecular Chemistry 15, № 4 (2017): 991–97. http://dx.doi.org/10.1039/c6ob02253g.

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23

Fujiwara, Shin-ichi, Masashi Toyofuku, Hitoshi Kuniyasu, and Nobuaki Kambe. "Transition-metal-catalyzed cleavage of carbon–selenium bond and addition to alkynes and allenes." Pure and Applied Chemistry 82, no. 3 (2010): 565–75. http://dx.doi.org/10.1351/pac-con-09-11-13.

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This account summarizes our recent results on transition-metal-catalyzed cleavage of C–Se bond and addition to unsaturated hydrocarbons such as alkynes and allenes. Pd(0)-catalyzed intramolecular carbamoselenation of alkynes forms four- to eight-membered α-alkylidenelactams. Interestingly, four-membered ring formation is faster than five- and six-membered ring formation. Intramolecular vinylselenation of suitably structured alkynes offers pathways to conjugated δ-lactam frameworks. Electron-withdrawing groups on the vinyl moiety are essential to promote this reaction. Intermolecular 1,2-additi

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24

Wagener, Tobias, Lukas Lückemeier, Constantin G. Daniliuc та Frank Glorius. "Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ‐Lactams". Angewandte Chemie International Edition 60, № 12 (2021): 6425–29. http://dx.doi.org/10.1002/anie.202016771.

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25

Samarat, Ali, Jihène Ben Kraïem, Taïcir Ben Ayed та Hassen Amri. "An efficient synthetic route to functionalized δ-lactams". Tetrahedron 64, № 40 (2008): 9540–43. http://dx.doi.org/10.1016/j.tet.2008.07.057.

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26

BOUDREAULT, N., R. G. BALL, C. BAYLY, M. A. BERNSTEIN та Y. LEBLANC. "ChemInform Abstract: Conformational Analysis of δ-Lactams (I)." ChemInform 25, № 47 (2010): no. http://dx.doi.org/10.1002/chin.199447032.

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27

Trenchs, Gisela, та Faïza Diaba. "Photoredox catalysis in the synthesis of γ- and δ-lactams from N-alkenyl trichloro- and dichloroacetamides". Organic & Biomolecular Chemistry 20, № 15 (2022): 3118–23. http://dx.doi.org/10.1039/d2ob00276k.

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28

Santhanam, Venkatesan, Pradeep Pant, B. Jayaram та Namakkal G. Ramesh. "Design, synthesis and glycosidase inhibition studies of novel triazole fused iminocyclitol-δ-lactams". Organic & Biomolecular Chemistry 17, № 5 (2019): 1130–40. http://dx.doi.org/10.1039/c8ob03084g.

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Synthesis of novel triazole fused iminocyclitol-δ-lactams, from tri-O-benzyl-d-glucal, involving intermolecular [3 + 2]cycloaddition and intramolecular lactamisation reactions as key steps is described.

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29

Casimir, J. Richard, Claude Didierjean, André Aubry, Marc Rodriguez, Jean-Paul Briand та Gilles Guichard. "Stereoselective Alkylation ofN-Boc-protected-5-substituted δ-Lactams: Synthesis ofα,δ-Disubstituted δ-Amino Acids". Organic Letters 2, № 7 (2000): 895–97. http://dx.doi.org/10.1021/ol9913136.

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30

López-Francés, Adrián, Xabier del Del Corte, Zuriñe Serna-Burgos, Edorta Martínez de Martínez de Marigorta, Francisco Palacios та Javier Vicario. "Exploring the Synthetic Potential of γ-Lactam Derivatives Obtained from a Multicomponent Reaction. Applications as Antiproliferative Agents". Molecules 27, № 11 (2022): 3624. http://dx.doi.org/10.3390/molecules27113624.

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A study on the reactivity of 3-amino α,β-unsaturated γ-lactam derivatives obtained from a multicomponent reaction is presented. Key features of the substrates are the presence of an endocyclic α,β-unsaturated amide moiety and an enamine functionality. Following different synthetic protocols, the functionalization at three different positions of the lactam core is achieved. In the presence of a soft base, under thermodynamic conditions, the functionalization at C-4 takes place where the substrates behave as enamines, while the use of a strong base, under kinetic conditions, leads to the formati

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31

Listro, Roberta, Giacomo Rossino, Serena Della Volpe та ін. "Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam, Useful Intermediate for the Synthesis of Bioactive Compounds". Molecules 25, № 24 (2020): 6023. http://dx.doi.org/10.3390/molecules25246023.

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During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (trans-1). For the preparation of racemic trans-1, the Castagnoli-Cushman reaction was employed. (Semi)-preparative enantioselective HPLC allowed to obtain enantiomerically pure trans-1 whose absolute configura

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32

Fujiki, Katsumasa. "Rhodium-Streptavidin Complex-Catalyzed Asymmetric Synthesis of δ-Lactams". Journal of Synthetic Organic Chemistry, Japan 78, № 6 (2020): 630–31. http://dx.doi.org/10.5059/yukigoseikyokaishi.78.630.

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33

Rodrı́guez, S., E. Castillo, M. Carda та J. A. Marco. "Synthesis of conjugated δ-lactams using ring-closing metathesis". Tetrahedron 58, № 6 (2002): 1185–92. http://dx.doi.org/10.1016/s0040-4020(01)01221-2.

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34

Feng, X., Z. Chen, L. Lin, D. Chen, J. Li та X. Liu. "Catalytic Enantioselective Preparation of α,β-Unsaturated δ-Lactams". Synfacts 2010, № 09 (2010): 1024. http://dx.doi.org/10.1055/s-0030-1257997.

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35

Beng, Timothy K., Morgan J. Rodriguez та Claire Borg. "Stereocontrolled access to δ-lactone-fused-γ-lactams bearing angular benzylic quaternary stereocenters". RSC Advances 12, № 27 (2022): 17617–20. http://dx.doi.org/10.1039/d2ra02167f.

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The catalytic halolactonization of readily affordable γ-lactam-tethered alkenoic acids has facilitated the site-selective, efficient, and stereocontrolled synthesis of halogenated fused γ-lactam-δ-lactones.

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36

Di Mola, Antonia, Caterina Vietri, Consiglia Tedesco та Antonio Massa. "Catalyst-Free Spontaneous Aza-Mannich/Lactamization Cascade Reaction: Easy Access to Polycyclic δ-Lactams". Molecules 30, № 13 (2025): 2702. https://doi.org/10.3390/molecules30132702.

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Ring-fused azacyclic compounds are important building blocks in the synthesis of natural products and pharmaceutical agents. Herein, we report an effective and valuable one-pot approach to obtaining polycyclic fused δ-lactams from readily available 2-formylphenyl acetate and diamines under catalyst-free and green conditions.

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37

Annadi, Krishna, та Andrew G. H. Wee. "Ceric ammonium nitrate oxidation of N-(p-methoxybenzyl)lactams: competing formation of N-(hydroxymethyl)δ-lactams". Arkivoc 2014, № 6 (2014): 108–26. http://dx.doi.org/10.3998/ark.5550190.p008.840.

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38

Albrecht, Anna, Fabio Morana, Alberto Fraile та Karl Anker Jørgensen. "Organophosphorus Reagents in Organocatalysis: Synthesis of Optically Active α-Methylene-δ-lactones and δ-Lactams". Chemistry - A European Journal 18, № 33 (2012): 10348–54. http://dx.doi.org/10.1002/chem.201201325.

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39

J.C. Martins, Frans, Agatha M. Viljoen, Hendrik G. Kruger, Johan A. Joubert та Philippus L. Wessels. "Synthesis of δ-lactams from pentacyclo[5.4.0.02,6.03,10.05,9]Undecane-8,11-dione". Tetrahedron 50, № 36 (1994): 10783–90. http://dx.doi.org/10.1016/s0040-4020(01)89270-x.

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40

Grison, Claude, Stéphane Genève та Philippe Coutrot. "Enantioselective synthesis of α,β-unsaturated γ- and δ-lactams". Tetrahedron Letters 42, № 23 (2001): 3831–34. http://dx.doi.org/10.1016/s0040-4039(01)00561-5.

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41

Seibel, Jürgen, David Brown, Augustin Amour, Simon J. Macdonald, Neil J. Oldham та Christopher J. Schofield. "Synthesis and evaluation of δ-Lactams (Piperazones) as elastase inhibitors". Bioorganic & Medicinal Chemistry Letters 13, № 3 (2003): 387–89. http://dx.doi.org/10.1016/s0960-894x(02)00995-2.

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42

Shen, De-Yang, Thi Ngan Nguyen, Shwu-Jen Wu та ін. "γ- and δ-Lactams from the Leaves of Clausena lansium". Journal of Natural Products 78, № 11 (2015): 2521–30. http://dx.doi.org/10.1021/acs.jnatprod.5b00148.

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43

Bhuma, Naresh, Madhuri Vangala, Roopa J. Nair, Sushma G. Sabharwal та Dilip D. Dhavale. "Halogenated d-xylono-δ-lactams: synthesis and enzyme inhibition study". Carbohydrate Research 402 (січень 2015): 215–24. http://dx.doi.org/10.1016/j.carres.2014.10.023.

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44

Cogswell, Thomas J., Craig S. Donald, De-Liang Long та Rodolfo Marquez. "ChemInform Abstract: Short and Efficient Synthesis of Fluorinated δ-Lactams." ChemInform 46, № 21 (2015): no. http://dx.doi.org/10.1002/chin.201521173.

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45

Casimir, J. Richard, Claude Didierjean, Andre Aubry, Marc Rodriguez, Jean-Paul Briand та Gilles Guichard. "ChemInform Abstract: Stereoselective Alkylation of N-Boc-Protected-5-substituted δ-Lactams: Synthesis of α,δ-Disubstituted δ-Amino Acids." ChemInform 31, № 27 (2010): no. http://dx.doi.org/10.1002/chin.200027190.

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46

Takahata, Hiroki, Tamotsu Takamatsu, Mayumi Mozumi, Yin-Shan Chen, Takao Yamazaki та Keiichi Aoe. "Highly selective iodine-induced lactam formation from γ,δ-unsaturated thioimidates. New entry to functionalized γ-lactams". J. Chem. Soc., Chem. Commun., № 21 (1987): 1627–29. http://dx.doi.org/10.1039/c39870001627.

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47

Squarcia, Antonella, Fabrizio Vivolo, Hans-Georg Weinig, Pietro Passacantilli та Giovanni Piancatelli. "Glycal-mediated syntheses of enantiomerically pure polyhydroxylated γ- and δ-lactams". Tetrahedron Letters 43, № 26 (2002): 4653–55. http://dx.doi.org/10.1016/s0040-4039(02)00852-3.

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48

Lindemann, Ute, Günther Reck, Dirk Wulff-Molder та Pablo Wessig. "Photocyclization of 4-oxo-4-phenyl-butanoyl amines to δ-lactams". Tetrahedron 54, № 11 (1998): 2529–44. http://dx.doi.org/10.1016/s0040-4020(98)00002-7.

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49

Brummond, Kay M., Thomas O. Painter, Donald A. Probst та Branko Mitasev. "Rhodium(I)-Catalyzed Allenic Carbocyclization Reaction Affording δ- and ε-Lactams". Organic Letters 9, № 2 (2007): 347–49. http://dx.doi.org/10.1021/ol062842u.

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50

Chiacchio, Ugo, Antonino Corsaro, Anna Piperno, Antonio Rescifina, Giovanni Romeo та Roberto Romeo. "ChemInform Abstract: Stereoselective Synthesis of Enantiomerically Pure Isoxazolidine-Fused δ-Lactams." ChemInform 30, № 26 (2010): no. http://dx.doi.org/10.1002/chin.199926151.

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