Design and synthesis of novel ring-expanded arbekacin analogues

Heterocycles

Volumn 71, Issue 8, 2007, Pages 1715-1721

  Minowa, Nobuto ^a   Hiraiwa, Yukiko ^a   Akiyama, Yoshihisa ^a   Maebashi, Kazunori ^a   Usui, Takayuki ^a   Ikeda, Daishiro ^b  

^a MEIJI SEIKA KAISHA LTD   (Japan)

^b INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35548940399     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-07-11081     Document Type: Article

References (25)

1. Magnet S., and Blanchard J.S. Chem. Rev. 105 (2005) 477
2. Carter A.P., Clemons W.M., Brodersen D.E., Morgan-Warren R.J., Wimberly B.T., and Ramakrishnan V. Nature 407 (2000) 340
3. Ogle J.M., Brodersen D.E., Clemons Jr. W.M., Tarry M.J., Carter A.P., and Ramakrishnan V. Science 292 (2001) 897
4. Vicens Q., and Westhof E. Structure 9 (2001) 647
5. Busscher G.F., Rutjes F.P.J.T., and Delft F.L. Chem. Rev. 105 (2005) 775
6. Castro S., Fyvie W.S., Hatcher S.A., and Peczuh M.W. Org. Lett. 7 (2005) 4709
7. Paquette L.A., and Zhang Y. Org. Lett. 7 (2005) 511
8. Li H., Bleriot Y., Mallet J.M., Garcia E.R., Vogel P., Zhang Y., and Sinay P. Tetrahedron: Asymmetry 16 (2005) 313
9. Minowa N., Akiyama Y., Hiraiwa Y., Maebashi K., Usui T., and Ikeda D. Bioorg. Med. Chem. Lett. 16 (2006) 6351
10. Kondo S., Iinuma K., Yamamoto H., Maeda K., and Umezawa H. J. Antibiotics 26 (1973) 412
11. Ubukata K., Yamashita N., Gotoh A., and Konno M. Antimicrob. Agents Chemother. 25 (1984) 754
12. 2O with KOH. S.R. Sandler and W. Karo, Organic Functional Group Preparations, Academic Press: New York, 1968; p395.
13. Weygand F., and Hunger K. Chem. Ber. 95 (1962) 1
14. Nagasawa T., Kuroiwa K., Narita K., and Isowa Y. Bull. Chem. Soc. Jpn 46 (1973) 1269
15. Albright J.D., and Goldman L. J. Am. Chem. Soc. 87 (1965) 4214
16. House H.O., Grubbs E.J., and Gannon W.F. MeOH accelerated the reaction of cyclohexanone with diazomethane. J. Am. Chem. Soc. 82 (1960) 4099
17. Bradley J.N., Cowell G.W., and Ledwith A. J. Chem. Soc. (1964) 4334
18. Electron-withdrawing or bulky groups attached to the α-positions of ketone, in addition to accelerating the reaction, usually increase the amount of oxide formed. In: Gutsche C.D. (Ed). Org. Reactions 8 (1954), Wiley and Sons, New York 364-429
19. 3), 72.5 (C-4"), 72.8 (C-2'"), 73.5 (C-5'), 74.6 (C-2"), 75.4 (C-5"), 81.0 (C-7), 83.2 (C-4), 98.1 (C-1'), 102.4 (C-1"), 157.2 (C-5), 179.1 (C-1'"). NMR assignments were made by interpretation of COSY experiments.
20. 4OH).
21. Marshall J.A., and Partridge J.J. J. Org. Chem. 33 (1968) 4090
22. Turro N.J., and Gagosian B. J. Am. Chem. Soc. 92 (1970) 2036
23. Mckinney M.A., and Patel P.P. J. Org. Chem. 38 (1973) 4064
24. MICs were detemined by the two-fold agar dilution method according to NCCLS.
25. Ardic N., Sareyyupoglu B., Ozyurt M., Hazunedaroglu T., and IIga U. Microbiological Research 161 (2006) 49