DOI QR코드

DOI QR Code

Glycidyl Tosylate is a Viable Starting Material for Oxazolidinone Antibacterials

  • Kim, Cho-Rom (Department of Chemistry, Ewha Womans University) ;
  • Ko, Soo-Y. (Department of Chemistry, Ewha Womans University)
  • Received : 2011.09.30
  • Accepted : 2011.10.17
  • Published : 2011.12.20

Abstract

Keywords

References

  1. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997, 30, 3.
  2. Zappia, G.; Gacs-Baits, E.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Current Organic Synthesis 2007, 4, 81. https://doi.org/10.2174/157017907779981552
  3. Zappia, G.; Cancelliere, G.; Gacs-Baitz, E.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Current Organic Synthesis 2007, 4, 238. https://doi.org/10.2174/157017907781369306
  4. Revies: Zappia, G.; Menendez, P.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Mini-Reviews in Medicinal Chemistry 2007, 7, 389. https://doi.org/10.2174/138955707780363783
  5. Vara Prasad, J. V. N. Current Opinion in Microbiology 2007, 10, 454. https://doi.org/10.1016/j.mib.2007.08.001
  6. Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, P. R.; Ulanowicz, D. A.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673. https://doi.org/10.1021/jm9509556
  7. Brickner, S. J.; Barbachyn, M. R.; Hutchinson, D. K.; Manninen, P. R. J. Med. Chem. 2008, 51, 1981. https://doi.org/10.1021/jm800038g
  8. Barbachyn, M. R.; Ford, C. W. Angew. Chem. Int. Ed. 2003, 42, 2010. https://doi.org/10.1002/anie.200200528
  9. Renslo, A. R.; Luehr, G. W.; Gordeev, M. F. Bioorg. Med. Chem. 2006, 14, 4227. https://doi.org/10.1016/j.bmc.2006.01.068
  10. Manninen, P. R.; Brickner, S. J. Org. Synth. 2005, 81, 112. https://doi.org/10.15227/orgsyn.081.0112
  11. Wang, C.-L. J.; Gregory, W. A.; Wuonola, M. A. Tetrahedron 1989, 45, 1323. https://doi.org/10.1016/0040-4020(89)80130-9
  12. Pearlman, B. A.; Perrault, W. R.; Barbachyn, M. R.; Manninen, P. R.; Toops, D. S.; Houser, D. J.; Fleck, T. J. US Patent 5837870, 1998.
  13. Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937. https://doi.org/10.1016/0040-4039(96)01835-7
  14. Perrault, W. R.; Pearlman, B. A.; Godrej, D. B.; Jeganathan, A.; Yamagata, K.; Chen, J. J.; Lu, C. V.; Herrington, P. M.; Gadwood, R. C.; Chan, L.; Lyster, M. A.; Maloney, M. T.; Moeslein, J. A.; Greene, M. L.; Barbachyn, M. R. Org. Process. Res. Dev. 2003, 7, 533. https://doi.org/10.1021/op034028h
  15. Yu, D. S.; Huang, L.; Liang, H.; Gong, P. Chinese Chem. Lett. 2005, 16, 875.
  16. Madhusudhan, G,; Om Reddy, G.; Rajesh, T.; Ramanatham, J.; Dubey, P. K. Tetrahedron Lett. 2008, 49, 3060. https://doi.org/10.1016/j.tetlet.2008.03.061
  17. Lohray, B. B.; Baskaran, S.; Srinivasa Rao, B.; Yadi Reddy, B.; Nageswara Rao, I. Tetrahedron Lett. 1999, 40, 4855. https://doi.org/10.1016/S0040-4039(99)00854-0
  18. Xu, G. Y.; Zhou, Y.; Xu, M. C. Chinese Chem. Lett. 2006, 17, 302.
  19. Kim, S. W.; Lee, J. G.; Lee, E. J.; Park Choo, H.-Y.; Yoo, C. Y.; Lee, D. Y.; Roh, K. R. Kim, E. K. J. Comb. Chem. 2004, 6, 851. https://doi.org/10.1021/cc0499237
  20. Moran-Ramallal, R.; Liz, R.; Gotor, V. Org. Lett. 2008, 10, 1935. https://doi.org/10.1021/ol800443p
  21. Narina, S. V.; Sudalai, A. Tetrahedron Lett. 2006, 47, 6799. https://doi.org/10.1016/j.tetlet.2006.07.065
  22. Song, L.; Chen, X.; Zhang, S.; Zhang, H.; Li, P.; Luo, G.; Liu, W.; Duan, W.; Wang, W. Org. Lett. 2008, 10, 5489. https://doi.org/10.1021/ol802333n
  23. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421. https://doi.org/10.1021/ar960061v
  24. Nielsen, L. P. C.; Jacobsen, E. N. in Aziridines and Epoxides in Organic Synthesis, Yudin, A. K., Ed., Wiley, 2006.
  25. Hanson, R. M. Chem. Rev. 1991, 91, 437. https://doi.org/10.1021/cr00004a001
  26. Klunder, J. M.; Onami, T.; Sharpless, K. B. J. Org. Chem. 1989, 54, 1295. https://doi.org/10.1021/jo00267a014
  27. Klunder, J. M.; Ko, S. Y.; Sharpless, K. B. J. Org. Chem. 1986, 51, 3710. https://doi.org/10.1021/jo00369a032
  28. Barton, D. L.; Press, J. B.; Hajos, Z. G.; Sawyers, R. A. Tetrahedron:Asym. 1992, 3, 1189. https://doi.org/10.1016/S0957-4166(00)82104-7
  29. Dyen, M. E.; Swern, D. Chem. Rev. 1967, 67, 197. https://doi.org/10.1021/cr60246a003
  30. Herweh, J. E. J. Org. Chem. 1968, 33, 4029. https://doi.org/10.1021/jo01275a007
  31. Herweh, J. E.; Kauffman, W. J. Tetrahedron Lett. 1971, 809.
  32. Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett. 1991, 248.
  33. Landini, D.; Albanese, D.; Penso, M. Tetrahedron 1992, 48, 4163. https://doi.org/10.1016/S0040-4020(01)92194-5
  34. Takle, A.; Kocienski, P. Tetrahedron 1990, 46, 4503. https://doi.org/10.1016/S0040-4020(01)85578-2
  35. Holte, P. T.; Thijs, L.; Zwanenburg, B. Org. Lett. 2001, 3, 1093. https://doi.org/10.1021/ol015723h
  36. Holte, P. T.; van Esseveldt, B. C. J.; Thijs, L.; Zwanenburg, B. Eur. J. Org. Chem. 2001, 2965.
  37. Alexander, R.; Ko, E. C. F.; Parker, A. J.; Broxton, T. J. J. Am. Chem. Soc. 1968, 90, 5049. https://doi.org/10.1021/ja01021a002

Cited by

  1. Palladium-Catalyzed Cyclization Reactions of 2,3-Allenyl Amines with Propargylic Carbonates vol.14, pp.9, 2012, https://doi.org/10.1021/ol3007293
  2. A New Method for the Oxazolidinone Key Intermediate of Linezolid and its Formal Synthesis vol.33, pp.4, 2012, https://doi.org/10.5012/bkcs.2012.33.4.1389
  3. Potential Pitfalls of Using Epichlorohydrin as Starting Material for Oxazolidinone Antibacterials vol.34, pp.2, 2013, https://doi.org/10.5012/bkcs.2013.34.2.641
  4. Synthesis of Oxazolidinones from Epoxides and Isocyanates Catalyzed by Rare-Earth-Metal Complexes vol.7, pp.7, 2015, https://doi.org/10.1002/cctc.201403015
  5. Synthesis of oxazolidinones: rhodium-catalyzed C–H amination of N-mesyloxycarbamates vol.15, pp.19, 2017, https://doi.org/10.1039/C7OB00378A