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Journal articles on the topic 'Δ-Lactams'

Author: Grafiati

Published: 25 January 2025

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1

Coullon, Héloise, Aline Rifflet, Richard Wheeler, Claire Janoir, Ivo Gomperts Boneca, and 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, no. 47 (September 28, 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. Using ultra-HPLC coupled with high-resolution MS, here we found that the spore cortex of the C. difficile 630Δerm strain differs from that of Bacillus subtilis. Among these differences, the muramic-δ-lactams represented only 24% in C. difficile, compared with 50% in B. subtilis. CD630_14300 and CD630_27190 were identified as genes encoding the C. difficile N-deacetylases PdaA1 and PdaA2, required for muramic-δ-lactam synthesis. In a pdaA1 mutant, only 0.4% of all muropeptides carried a muramic-δ-lactam modification, and muramic-δ-lactams were absent in the cortex of a pdaA1–pdaA2 double mutant. Of note, the pdaA1 mutant exhibited decreased sporulation, altered germination, decreased heat resistance, and delayed virulence in a hamster infection model. These results suggest a much greater role for muramic-δ-lactams in C. difficile than in other bacteria, including B. subtilis. In summary, the spore cortex of C. difficile contains lower levels of muramic-δ-lactams than that of B. subtilis, and PdaA1 is the major N-deacetylase for muramic-δ-lactam biosynthesis in C. difficile, contributing to sporulation, heat resistance, and virulence.

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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 butyrolactone (27). The structures of model γ- and δ-lactams 6, 7, and 8 have been determined at the B3LYP/6-31G(d) level of theory and the γ-lactams are much more twisted than the acyclic N,N-dimethoxyacetamide (5) resulting in a computed amidicity for 6 of only 25 % that of N,N-dimethylacetamide (3). The HERON reactions of N,N-dimethoxyacetamide (5) and alicyclic models 6 and 8 have been modelled computationally. The facile ring opening of 6 (EA = 113 kJ mol–1) and ring contraction of 8 (EA = 145 kJ mol–1) are predicted well, when compared with the HERON rearrangement of 5 (EA = 178 kJ mol–1).

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3

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

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4

Wang, Xin, Jia Lei, Guofeng Li, Jianping Meng, Chen Li, Jiazhu Li, and Kai Sun. "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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5

Domingo, Luis R., and 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, no. 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, and 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, no. 9 (April 28, 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 either their yield or their diastereoselectivity. Some of the lactams prepared in this work were evaluated for their hemolytic and cytotoxic responses. All compounds were found to be non-hemolytic at the tested concentration, indicating their safety profile in terms of blood cell integrity. Meanwhile, they exhibited interesting cytotoxicity responses that depend on both their lactam structure and cell line. Among the molecules tested, γ-lactam 2a exhibited the lowest IC50 values (100–250 µg/mL) as a function of its cell line, with promising selectivity against squamous carcinoma cells (A431) in comparison with fibroblasts (3T3 cell line).

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8

Albrecht, Anna, Łukasz Albrecht, and Tomasz Janecki. "Recent Advances in the Synthesis of α-Alkylidene-Substituted δ-Lactones, γ-Lactams and δ-Lactams." European Journal of Organic Chemistry 2011, no. 15 (April 14, 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, Tom W. Rademacher, Linda E. Fellows, Robert J. Nash, Donovan St C. Green, and Bryan Winchester. "δ-Lactams: synthesis fromD-glucose, and preliminiary evaluation as a fucosidase inhibitor, ofL-fuconic-δ-lactam." J. Chem. Soc., Chem. Commun., no. 7 (1988): 483–85. http://dx.doi.org/10.1039/c39880000483.

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10

Gan, Miaomiao, Lan Jiang, and Zhengning Li. "Diastereoselective Synthesis of γ-Lactams and δ-Lactams via a Conjugate Addition-Initiated Tandem Reaction." Synlett 30, no. 12 (May 20, 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, and Rodolfo Marquez. "Short and efficient synthesis of fluorinated δ-lactams." Organic & Biomolecular Chemistry 13, no. 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, and Tomasz Janecki. "ChemInform Abstract: Recent Advances in the Synthesis of α-Alkylidene-Substituted δ-Lactones, γ-Lactams and δ-Lactams." ChemInform 42, no. 41 (September 19, 2011): no. http://dx.doi.org/10.1002/chin.201141234.

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14

Gnilka, Radoslaw, and Czeslaw Wawrzeńczyk. "Synthesis of Sabina δ-Lactones and Sabina δ-Lactams from (+)-Sabinene." Australian Journal of Chemistry 66, no. 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 obtained by Beckmann rearrangement of sabina ketone oximes 5a and 5b. An attempt to separate (–)-sabina ketone oximes 5a and 5b is also presented.

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15

Albrecht, Łukasz, Bo Richter, Henryk Krawczyk, and Karl Anker Jørgensen. "Enantioselective Organocatalytic Approach to α-Methylene-δ-lactones and δ-Lactams." Journal of Organic Chemistry 73, no. 21 (November 7, 2008): 8337–43. http://dx.doi.org/10.1021/jo801582t.

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16

Schmidt, Johannes Philipp, and 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, no. 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, and 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, no. 7 (2014): 949–52. http://dx.doi.org/10.1039/c4md00162a.

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18

Alves, Nuno G., Américo J. S. Alves, Maria I. L. Soares, and Teresa M. V. D. Pinho e Melo. "Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams." Advanced Synthesis & Catalysis 363, no. 10 (April 7, 2021): 2464–501. http://dx.doi.org/10.1002/adsc.202100013.

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19

He, Chonglong, Yipeng Zhou, Zhanhuan Li, Jianfeng Xu, and 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, no. 7 (2021): 1569–74. http://dx.doi.org/10.1039/d0qo01489c.

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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

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

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22

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

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23

BOUDREAULT, N., R. G. BALL, C. BAYLY, M. A. BERNSTEIN, and Y. LEBLANC. "ChemInform Abstract: Conformational Analysis of δ-Lactams (I)." ChemInform 25, no. 47 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199447032.

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24

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

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25

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 (February 18, 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-addition of selenol esters onto allenes proceeds with excellent regioselectivity and high stereoselectivity in the presence of a Pd(0) catalyst, producing functionalized allyl selenides. In addition, Pd(0)-catalyzed intramolecular selenocarbamoylation of allenes gives α,β-unsaturated γ- and δ-lactams with perfect regioselectivity. The scope and limitations, as well as reaction pathways, are discussed.

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26

Sun, Baomin, Lijiu Gao, Shide Shen, Chenxia Yu, Tuanjie Li, Yuanwei Xie, and Changsheng Yao. "NHC-catalyzed [4 + 2] annulation of 2-bromo-2-enals with acylhydrazones: enantioselective synthesis of δ-lactams." Organic & Biomolecular Chemistry 15, no. 4 (2017): 991–97. http://dx.doi.org/10.1039/c6ob02253g.

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27

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

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28

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

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29

Santhanam, Venkatesan, Pradeep Pant, B. Jayaram, and Namakkal G. Ramesh. "Design, synthesis and glycosidase inhibition studies of novel triazole fused iminocyclitol-δ-lactams." Organic & Biomolecular Chemistry 17, no. 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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30

López-Francés, Adrián, Xabier del Del Corte, Zuriñe Serna-Burgos, Edorta Martínez de Martínez de Marigorta, Francisco Palacios, and Javier Vicario. "Exploring the Synthetic Potential of γ-Lactam Derivatives Obtained from a Multicomponent Reaction. Applications as Antiproliferative Agents." Molecules 27, no. 11 (June 5, 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 formation of C-5-functionalized γ-lactams, in the presence of ethyl glyoxalate, through a highly diastereoselective vinylogous aldol reaction. Moreover, the nucleophilic addition of organometallic species allows the functionalization at C-3, through the imine tautomer, affording γ-lactams bearing tetrasubstituted stereocenters, where the substrates act as imine electrophiles. Taking into account the advantage of the presence of a chiral stereocenter in C-5 substituted γ-lactams, further diastereoselective transformations are also explored, leading to novel bicyclic substrates holding a fused γ and δ-lactam skeleton. Remarkably, an example of a highly stereoselective formal [3+3] cycloaddition reaction of chiral γ-lactam substrates is reported for the synthesis of 1,4-dihidropyridines, where a non-covalent attractive interaction of a carbonyl group with an electron-deficient arene seems to drive the stereoselectivity of the reaction to the exclusive formation of the cis isomer. In order to unambiguously determine the substitution pattern resulting from the diverse reactions, an extensive characterization of the substrates is detailed through 2D NMR and/or X-ray experiments. Likewise, applications of the substrates as antiproliferative agents against lung and ovarian cancer cells are also described.

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31

Listro, Roberta, Giacomo Rossino, Serena Della Volpe, Rita Stabile, Massimo Boiocchi, Lorenzo Malavasi, Daniela Rossi, and Simona Collina. "Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam, Useful Intermediate for the Synthesis of Bioactive Compounds." Molecules 25, no. 24 (December 19, 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 configuration was assigned by X-ray diffractometry. Compound (+)-(2R,3R)-1 represents a reference compound for the configurational study of structurally related lactams.

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32

Fujiki, Katsumasa. "Rhodium-Streptavidin Complex-Catalyzed Asymmetric Synthesis of δ-Lactams." Journal of Synthetic Organic Chemistry, Japan 78, no. 6 (June 1, 2020): 630–31. http://dx.doi.org/10.5059/yukigoseikyokaishi.78.630.

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33

Rodrı́guez, S., E. Castillo, M. Carda, and J. A. Marco. "Synthesis of conjugated δ-lactams using ring-closing metathesis." Tetrahedron 58, no. 6 (February 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, and X. Liu. "Catalytic Enantioselective Preparation of α,β-Unsaturated δ-Lactams." Synfacts 2010, no. 09 (August 23, 2010): 1024. http://dx.doi.org/10.1055/s-0030-1257997.

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35

Beng, Timothy K., Morgan J. Rodriguez, and Claire Borg. "Stereocontrolled access to δ-lactone-fused-γ-lactams bearing angular benzylic quaternary stereocenters." RSC Advances 12, no. 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

Annadi, Krishna, and Andrew G. H. Wee. "Ceric ammonium nitrate oxidation of N-(p-methoxybenzyl)lactams: competing formation of N-(hydroxymethyl)δ-lactams." Arkivoc 2014, no. 6 (November 20, 2014): 108–26. http://dx.doi.org/10.3998/ark.5550190.p008.840.

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37

Albrecht, Anna, Fabio Morana, Alberto Fraile, and Karl Anker Jørgensen. "Organophosphorus Reagents in Organocatalysis: Synthesis of Optically Active α-Methylene-δ-lactones and δ-Lactams." Chemistry - A European Journal 18, no. 33 (June 15, 2012): 10348–54. http://dx.doi.org/10.1002/chem.201201325.

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38

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

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39

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

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40

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

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41

Shen, De-Yang, Thi Ngan Nguyen, Shwu-Jen Wu, Young-Ji Shiao, Hsin-Yi Hung, Ping-Chung Kuo, Daih-Huang Kuo, Tran Dinh Thang, and Tian-Shung Wu. "γ- and δ-Lactams from the Leaves of Clausena lansium." Journal of Natural Products 78, no. 11 (November 2, 2015): 2521–30. http://dx.doi.org/10.1021/acs.jnatprod.5b00148.

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42

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

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43

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

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44

Casimir, J. Richard, Claude Didierjean, Andre Aubry, Marc Rodriguez, Jean-Paul Briand, and Gilles Guichard. "ChemInform Abstract: Stereoselective Alkylation of N-Boc-Protected-5-substituted δ-Lactams: Synthesis of α,δ-Disubstituted δ-Amino Acids." ChemInform 31, no. 27 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200027190.

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45

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

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46

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

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47

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

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

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Chiacchio, Ugo, Antonino Corsaro, Anna Piperno, Antonio Rescifina, Giovanni Romeo, and Roberto Romeo. "ChemInform Abstract: Stereoselective Synthesis of Enantiomerically Pure Isoxazolidine-Fused δ-Lactams." ChemInform 30, no. 26 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199926151.

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Rodriguez, S., E. Castillo, M. Carda, and J. A. Marco. "ChemInform Abstract: Synthesis of Conjugated δ-Lactams Using Ring-Closing Metathesis." ChemInform 33, no. 28 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200228170.

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