Słowa kluczowe

Informacje szczegółowe

Kategoria:

Publikacja w czasopiśmie

Typ:

artykuł w czasopiśmie wyróżnionym w JCR

Opublikowano w:

SYNTHETIC COMMUNICATIONS nr 48, strony 1793 - 1804,
ISSN: 0039-7911

Język:

angielski

Rok wydania:

2018

Opis bibliograficzny:

Zakaszewska A., Najda-Mocarska E., Makowiec S.: Preparation of bicyclic β-lactam and bicyclic 1,3- oxazinone scaffolds using combined cycloaddition and metathesis processes// SYNTHETIC COMMUNICATIONS. -Vol. 48, nr. 14 (2018), s.1793-1804

DOI:

Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1080/00397911.2018.1465980

Bibliografia: test

1. Dougherty, T. J.; Pucci, M. J. Antibiotic Discovery and Development, Springer: New York, 2012. (b) Morin, R. B.; Gorman, M. Chemistry and Biology of β-Lactam Antibiotics, Academic Press: New York, 1982.
2. Torok, M. E.; Moran, E.; Cooke, F. Oxford Handbook of Infectious Diseases and Microbiology, 1 st ed., Oxford University Press, 2009. otwiera się w nowej karcie
3. Staudinger, H. Zur Kenntniss der Ketene. Diphenylketen. Justus Liebigs Ann. Chem. 1907, 356, 51-123. otwiera się w nowej karcie
4. Bruggink, A. Synthesis of β-lactam antibiotics: chemistry, biocatalysis and process integration, Kluwer Academic Publishers, 2001. otwiera się w nowej karcie
5. Curran, W. V.; Ross, A. A.; Lee, V. J. N-azamonobactams. 1. The synthesis of some 3-substituted N-azamonobactam derivatives. J. Antibiot. 1988, 41, 1418-1429. b) otwiera się w nowej karcie
6. Indelicato, J. M.; Fisher, J. W.; Pasini, C. E. Intramolecular nucleophilic amino attack in a monobactam: synthesis and stability of (2S,3S)-3-[(2R)-2-amino-2-phenylacetamido]-2- methyl-4-oxo-1-azetidine sulfo nic acid. J. Pharm. Sci. 1986, 75, 304-306. otwiera się w nowej karcie
7. Gupta, E. K.; Ito, M. K. Ezetimibe: the first in a novel class of selective cholesterol- absorption inhibitors. Heart Dis. 2002, 4, 399-409. b) Clader, J. W. The discovery of ezetimibe: a view from outside the receptor. J. Med. Chem. 2004, 47, 1-9. c) Rosenblum, S. B.; Huynh, T.; Afonso, A. ; Davis, H. R.; Yumibe, N.; Clader, J. W.; Burnett, D. A. Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4 - hydroxyphenyl)-2-azetidinone (SCH 58235): a designed, potent, orally active inhibitor of cholesterol absorption. J. Med. Chem. 1998, 41, 973-980. 11
8. Karlsson, S.; Sorensen, J. H.; Selection and Development of a Route for Cholesterol Absorption Inhibitor AZD4121. Org. Process Res. Dev. 2012, 16, 586-594. otwiera się w nowej karcie
9. Kramer, W.; Corsiero, D.; Girbig, F.; Jähne, G. Rabbit small intestine does not contain an annexin II/caveolin 1 complex as a target for 2-azetidinone cholesterol absorption inhibitors. Biochim. Biophys. Acta 2006, 1, 45-54. otwiera się w nowej karcie
10. Salisbury, B. G.; Davis, H. R.; Burrier, R. E.; Burnett, D. A.; Boykow, G. Caplen, M. otwiera się w nowej karcie
11. A.; Clemmons, A. L.; Compton, D. S.; Hoos, L. M.; McGregor, D. G.; Schnitzer-Polokoff, R.; Smith, A. A.; Weig, B. C.; Zilli, D. L.; Clader, J. W.; Sybertza, E. J. Hypocholesterolemic activity of a novel inhibitor of cholesterol absorption, SCH 48461. Atherosclerosis, 1995, 115, 45-63.
12. Grieco, P. A; Flynn, D. L.; Zelle, R. E. Beta.-Lactam antibiotics: a formal stereocontrolled total synthesis of (.+-.)-thienamycin. J. Am. Chem. Soc. 1984, 106, 6414- 6417. (b) Kametani, T.; Chu, S. D.; Honda, T. Asymmetric Synthesis of 4-Acetoxy-3- hydroxyethylazetidin-2-one, a Key Intermediate for the Preparation of Penem and Carbapenem Antibiotics. Heterocycles 1987, 25, 241-244. (c) Ito, K.; Iida, T.; Fujita, T.; Tsjui, S. A Simple Method for the Synthesis of Amides by Use of 2,2′-Dibenzothiazolyl Disulfide as an Oxidant. Synthesis 1981, 4, 287-288. (d) Palomo, C.; Azipurua, J. M.; Urchegui. R.; Iturburu, M.; Ochoa de Retana, A.; Cuevas. C. A convenient method for .beta.- lactam formation from .beta.-amino acids using phenyl phosphorodichloridate reagent. J. Org. Chem. 1991, 56, 2244-2247.
13. Gilman, H.; Speeter, M. The Reformatsky Reaction with Benzalaniline. J. Am. otwiera się w nowej karcie
14. Chem. Soc. 1943, 65, 2255-2256. (b) Ojima, I.; Habus, I.; Zhao, M.; Georg, G. I.; Jayasinghe, L.R. Efficient and practical asymmetric synthesis of the taxol C-13 side chain, N-benzoyl- (2R,3S)-3-phenylisoserine, and its analogs via chiral 3-hydroxy-4-aryl-.beta.-lactams through 12 otwiera się w nowej karcie
15. chiral ester enolate-imine cyclocondensation. J. Org. Chem. 1991, 56, 1681-1683. (c) Hart, D. otwiera się w nowej karcie
16. J.; Ha, D-C. The ester enolate-imine condensation route to .beta.-lactams. Chem. Rev. 1989, 89, 1447-1465. (d) Ojima, I.; Habus, I. Asymmetric synthesis of β-lactams by chiral ester enolate -imine condensation. Tetrahedron Lett. 1990, 31, 4289-4292. (e) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y.; Sun, C.; Brigaud, T. New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method. Tetrahedron 1992, 48, 6985-7012. (f) Ojima, I.; Habus, I.; Zhao, M. Efficient and practical asymmetric synthesis of the taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogs via chiral 3-hydroxy-4-aryl-.beta.-lactams through chiral ester enolate-imine cyclocondensation. J. Org. Chem. 1991, 56, 1681-1683. (g) Ojima, I.; Slater, J. S.; Kuduk, S.
17. D.; Takeuchi, C. S.; Gimi, R. H.; Sun, C. M.; Park, Y. H.; Pera, P.; Veith, J. M.; Bernacki, R.
18. J. Syntheses and Structure−Activity Relationships of Taxoids Derived from 14β-Hydroxy-10- deacetylbaccatin III J. Med. Chem. 1997, 40, 267-278.
19. Kinugasa, M.; Hashimot, S. The reactions of copper(I) phenylacetylide with nitrones. J. Chem. Soc. Chem. Commun. 1972, 8, 466-467. (b) Stecko, S.; Furman, B.; Chmielewski, M. Kinugasa reaction: an 'ugly duckling' of β-lactam chemistry Tetrahedron 2014, 70, 7817-7844.
20. Chmielewski, M.; Kałuza, Z.; Abramski, W.; Bełzacki C. Stereocontrolled entry to 1- oxapenams and 1-oxacephems from carbohydrates. Tetrahedron Lett. 1987, 28, 3035-3038. otwiera się w nowej karcie
21. Kamath, A.; Ojima, I. Advances in the chemistry of β-lactam and its medicinal applications. Tetrahedron 2012, 68, 10640-10664. (b) Mendez, L.; Mata, E. G. Synthesis of Multicyclic β-Lactam Derivatives via Solid-Phase-Generated Ketenes. J. Comb. Chem. 2010, 12, 810-813. (c) Jiao, L.; Zhang, Q.; Liang, Y.; Zhang, S.; Xu, J. A Versatile Method for the Synthesis of 3-Alkoxycarbonyl β-Lactam Derivatives J. Org. Chem. 2006, 71, 815-818. (d) 13
22. Xu, J. Synthesis of β-lactams with π electron-withdrawing substituents. Tetrahedron Synthesis of β-lactams with π electron-withdrawing substituents. 2012, 68, 10696-10747. (e) otwiera się w nowej karcie
23. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. The Development of the First Catalyzed Reaction of Ketenes and Imines: Catalytic, Asymmetric Synthesis of β- otwiera się w nowej karcie
24. Lactams. J. Am. Chem. Soc. 2002, 124, 6626-6635. (e) McKittrick, B. A.; Ma, K.; Huie, K.; Yumibe, N.; Davis, H.; Clader, J. W.; Czarnecki, M.; McPhail A. T. Synthesis of C3
25. Heteroatom-Substituted Azetidinones That Display Potent Cholesterol Absorption Inhibitory Activity. J. Med. Chem. 1998, 41, 752-759. (f) Li, B.; Wang, Y.; Du, D. M.; Xu, J. Notable and Obvious Ketene Substituent-Dependent Effect of Temperature on the Stereoselectivity in the Staudinger Reaction. J. Org. Chem. 2007, 72, 990-997. (g) Nahmany, M.; Melman, A. Simple Approach to β-Lactam Derivatives from N-Acylimidazoles. J. Org. Chem. 2006, 71, 5804-5806.
26. Janikowska, K.; Pawelska, P.; Makowiec, S. One-Step Synthesis of β-Lactams with Retro-Amide Side Chain. Synthesis, 2011, 1, 69-72. (b) Zakaszewska, A.; Najda, E.; Makowiec, S. The stereoselective formation of β-lactams with acyl ketenes generated from 5- acyl-Meldrum's acids. New. J. Chem. 2016, 40, 6546-6549. (c) Zakaszewska, A.; Najda-
27. Mocarska, E.; Makowiec, S.; Evidence for an umpolung type of [2+2] cycloaddition of 2- carbamoyl ketenes. New. J. Chem. 2017, 41, 6067-6070. (d) Zakaszewska, A.; Najda-
28. Mocarska, E.; Makowiec, S. A new approach to the stereoselective synthesis of trans-3- carbamoyl-β-lactam moieties New. J. Chem. 2017, 41, 2479-2489.
29. Yamamoto, Y.; Watanabe, Y. 1,3-Oxazines and Related Compounds. XIV. Facile Synthesis of 2,3,6-Trisubstituted 2,3-Dihydro-1,3-oxazine-5-carboxylic Acids and 1,4- Disubstituted 3-Acyl-β-lactams from Acyl Meldrum's Acids and Schiff Bases Chem. Pharm. Bull. 1987, 35, 1871-1878. otwiera się w nowej karcie
30. Emtenäs, H.; Soto, G.; Hultgren, S. J.; Marshall, G. R.; Almqvist, F. Stereoselective synthesis of optically active beta-lactams, potential inhibitors of pilus assembly in pathogenic bacteria. Org. Lett. 2000, 2, 2065-2067. otwiera się w nowej karcie
31. Pemberton, N.; Emtenäs, H.; Boström, D.; Domaille, P. J.; Greenberg, W. A.; Levin, otwiera się w nowej karcie
32. M. D.; Zhu, Z.; Almqvist, F. Cycloaddition of delta2-thiazolines and acyl ketenes under acidic conditions results in bicyclic 1,3-oxazinones and not 6-acylpenams as earlier reported. Org. otwiera się w nowej karcie
33. Lett. 2005, 7, 1019-1021.
34. Emtenäs, H.; Alderin, L.; Almqvist, F. An enantioselective ketene-imine cycloaddition method for synthesis of substituted ring-fused 2-pyridinones. J. Org. Chem. 2001, 66, 6756-6761. (b) Pemberton, N.; Aberg, V.; Almstesdt, H.; Westermark, A.; Almqvist, F. Microwave-assisted synthesis of highly substituted aminomethylated 2- pyridones. J. Org. Chem. 2004, 69, 7830-7835. (c) Emtenäs, H.; Carlsson, M.; Pinkner, S. J.; Hultgren S. J.; Almqvist, F. Stereoselective synthesis of optically active bicyclic beta-lactam carboxylic acids that target pilus biogenesis in pathogenic bacteria. Org. Biomol. Chem. 2003, 1, 1308-1314. (d) Chorell, E.; Pinkner, J. S.; Phan, G.; Edvinsson, S.; Buelens, F.; Remaut, H.; Waksman, G.; Hultgren, S. J.; Almqvist, F. Design and Synthesis of C-2 Substituted Thiazolo and Dihydrothiazolo Ring-Fused 2-Pyridones: Pilicides with Increased Antivirulence Activity. J. Med. Chem. 2010, 53, 5690-5695. (e) Emtenäs, H.; Pinkner, S. J.; Jones, M. J.; Jakobsson, L.; Hultgren, S. J.; Almqvist, F. Functionalization of bicyclic 2- pyridones targeting pilus biogenesis in uropathogenic Escherichia coli. Tetrahedron Lett. 2007, 48, 4543-4546.
35. Yamamoto, Y.; Watanabe, Y.; Ohnishi, S. 1, 3-Oxazines and Related Compounds. otwiera się w nowej karcie
36. XIII. Reaction of Acyl Meldrum's Acids with Schiff Bases Giving 2, 3-Disubstituted 5-Acy1- 3, 4, 5, 6-tetrahydro-2H-1, 3-oxazine-4, 6-diones and 2, 3, 6-Trisubstituted 2, 3-Dihydro-1, 3- 15 otwiera się w nowej karcie
37. oxazin-4-ones. Chem. Pharm. Bull. 1987, 35, 1860-1870. (b) Makowiec, S.; Najda, E.; Janikowska, K. Thermal Decomposition of Carbamoyl Meldrum's Acids: A Starting Point for the Preparation of 1,3-Oxazine Derivatives. J. Heterocycl. Chem. 2015, 52, 205-210. otwiera się w nowej karcie
38. Punda, P.; Makowiec, S. One-Step Formation of N-Alkenyl-malonamides and N- otwiera się w nowej karcie
39. Alkenyl-thiomalonamides from Carbamoyl Meldrum's Acids. Synth. Commun. 2013, 43, 1362-1367. otwiera się w nowej karcie
40. De Kimpe, N.; De Smaele, D.; Hofkens, A.; Dejaegher, Y.; Kesteleyn, B. Synthesis of 3-alkenylamines, 4-alkenylamines and 3-allenylamines via a transamination procedure. Tetrahedron 1997, 53, 10803-10816. (b) Smith, J. K.; Bergbreiter, D. E.; Newcomb, M. Formation and isomerization of 2-azaallyllithium reagents in deprotonations of N-benzyl ketimines containing .alpha.-protons. J. Org. Chem. 1985, 50, 4549-4553. otwiera się w nowej karcie
41. Tarling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D.; β-, γ-and δ- Lactams as conformational constraints in ring-closing metathesis. J. Chem. Soc., Perkin Trans. 1 1999, 1695-1702. (b) Barrett, A. G. M.; Baugh, S. P. D.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A. Enyne metathesis for the facile synthesis of highly functionalisednovel bicyclic β-lactams. Chem. Commun. 1997, 15, 1375-1376. (c) Barrett, A.
42. G. M.; Ahmed, M.; Baker, S. P.; Baugh, S. P. D.; Braddock, D. C.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. Tandem Ireland−Claisen Rearrangement Ring-Closing Alkene Metathesis in the Construction of Bicyclic β-Lactam Carboxylic Esters. J. Org. Chem. 2000, 65, 3716-3721. (d) Watson, K. D.; Carosso, S.; Miller, M. J. New and Concise Syntheses of the Bicyclic Oxamazin Core Using an Intramolecular Nitroso Diels-Alder Reaction and Ring- Closing Olefin Metathesis. Org. Lett. 2013, 15, 358-361. (e) Desroy, N.; Robert-Peillard, F.; Toueg, J.; Duboc, R.; Hénaut, Ch.; Rager, M-N.; Savignac, M.; Genêt, J-P. An Efficient Route to 4/5/6 Polycyclic β-Lactams. Eur. J. Org. Chem. 2004, 23, 4840-4849. (f) Woźnica, 16
43. M.; Masnyk, M.; Stecko, S.; Mames, A.; Furman, B.; Chmielewski, M.; Frelek, J.
44. Structure−Chiroptical Properties Relationship of Carbapenams by Experiment and Theory. J. Org. Chem. 2010, 75, 7219-7226.
45. Katz, T.J.; Sivavec, T. M. Metal-catalyzed rearrangement of alkene-alkynes and the stereochemistry of metallacyclobutene ring opening. J. Am. Chem. Soc. 1985, 107, 737- otwiera się w nowej karcie
46. Kim, S. H.; Bowden, N.; Grubbs, R. H. Catalytic Ring Closing Metathesis of Dienynes: Construction of Fused Bicyclic Rings. J. Am. Chem. Soc. 1994, 116, 10801-10802. otwiera się w nowej karcie
47. Stragies, R.; Schuster, M.; Blechert, S. A Crossed Yne-Ene Metathesis Showing Atom Economy. Angew. Chem., Int. Ed. 1997, 36, 2518-2520. otwiera się w nowej karcie
48. Boyer, N.; Gloanec, P.; Nanteuil, G.; Jubaulta, P.; Quiriona, J. Ch. Chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams from ethylbromodifluoroacetate and imines during Reformatsky reaction. Tetrahedron 2007, 63, 12352-12366. otwiera się w nowej karcie

więcej (48) mniej

Weryfikacja:

Politechnika Gdańska