DOI QR코드

DOI QR Code

Spiro-β-lactams Synthesized from Imines Derived from 8-Azabicyclo[3.2.1]octan-3-ones

  • Received : 2014.07.08
  • Accepted : 2014.08.14
  • Published : 2014.12.20

Abstract

Keywords

References

  1. Fodor, G. Chemistry of the Alkaloids; Pelletier, S. W., Ed.; Van Nostrand-Reinhold: Princeton, New Jersey, 1970; Chapter 15.
  2. Fodor, G.; Janzso, G.; Dobo, P.; Koczor, J. Abh. Disch. Akad. Wiss. Berlin, Kl. Chem. Geol. Biol. 1964, 187.
  3. De La Camp, U. O.; Bottini, A. T.; Thut, C. C.; Gal, J.; Bellettini, A. G. J. Org. Chem. 1972, 37, 324. https://doi.org/10.1021/jo00967a034
  4. Wiger, G. R.; Rettig, M. F. J. Am. Chem. Soc. 1976, 98, 4168. https://doi.org/10.1021/ja00430a027
  5. Trigo, G. G.; Martines, M. Pharm. Mediaterr. 1974, 10, 643.
  6. Sacristan, A. G.; Illera, M.; Sancher, F. S. Arch. Formcol. Toxicol. 1977, 3, 57.
  7. Trigo, G. G.; Martinez, E. J. Pharm. Sci. 1981, 70, 87. https://doi.org/10.1002/jps.2600700118
  8. Izquierdo, M. L.; Galvez, E.; Burgos, C.; Florencio, F. J. Heterocyclic Chem. 1988, 25, 419. https://doi.org/10.1002/jhet.5570250213
  9. (a) The Organic Chemistry of ${\beta}$-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
  10. (b) Nau, R.; Eiffert, A. Clin. Microb. Rev. 2002, 15, 95. https://doi.org/10.1128/CMR.15.1.95-110.2002
  11. (a) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Luckacs, G., Ohno, M., Eds.; Springer: Berlin, 1990.
  12. (b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Pure Appl. Chem. 2000, 72, 1763.
  13. (c) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813.
  14. (a) Strauss, A.; Otto, H. H. Helv. Chim. Acta 1997, 80, 1823. https://doi.org/10.1002/hlca.19970800606
  15. (b) Anklam, S.; Liebscher, J. Tetrahedron 1998, 54, 6369. https://doi.org/10.1016/S0040-4020(98)00296-8
  16. (c) Dalla-Croce, P.; La Rosa, C. Tetrahedron: Asymmetry 1999, 10, 1193. https://doi.org/10.1016/S0957-4166(99)00096-8
  17. (d) Barba, V.; Hernandez, C.; Rojas-Lima, S.; Farfan, N.; Santillan, R. Can. J. Chem. 1999, 77, 2025. https://doi.org/10.1139/v99-212
  18. (e) Papillon, J. P. B.; Taylor, R. J. K. Org. Lett. 2000, 2, 1987. https://doi.org/10.1021/ol0058792
  19. (f) Arjona, O.; Csaky, A. G.; Murcia, C.; Plumet, J. Tetrahedron Lett. 2002, 43, 6405. https://doi.org/10.1016/S0040-4039(02)01375-8
  20. (a) Yamamoto, Y.; Asao, N.; Tsukuda, N. In Advances in Asymmetric Synthesis; Hassner, A. H., Ed.; Asymmetric Synthesis of ${\beta}$-Aminoacids and ${\beta}$-Lactam Derivatives via Conjugate Addition of Metal Amides. JAI Press: Stamford, CT, 1998; Vol. 3.
  21. (b) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675. https://doi.org/10.1021/cr960433d
  22. (c) Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2000, 563.
  23. (d) Mata, E. G. Curr. Pharm. Des. 1999, 5, 955.
  24. Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223.
  25. Jung, D. I.; Park, J. H.; Roh, S. A.; Lee, Y. G.; Park, Y. M.; Kim, I. S.; Jeong, I. S.; Park, M. S. J. Korean Chem. Soc. 1997, 41, 414.
  26. Jung, D. I.; Park, J. H.; Park, C. S.; Kim, Y. Y.; Jung, D. H.; Kim, I. S.; Park, M. S. J. Korean Chem. Soc. 1999, 43, 122.
  27. Jung, D. I.; Park, C. S.; Kim, Y. H.; Lee, D. H.; Lee, Y. G.; Park, Y. M.; Choi, S. K. Synth. Commun. 2001, 31, 3255. https://doi.org/10.1081/SCC-100106034
  28. Jung, D. I.; Song, J. H.; Kim, Y. H.; Lee, D. H.; Song, H. A.; Lee, Y. G.; Park, Y. M.; Choi, S. K.; Hahn, J. T.; Cho, S. J. Bull. Korean Chem. Soc. 2004, 25, 1932. https://doi.org/10.5012/bkcs.2004.25.12.1932
  29. Jung, D. I.; Song, J. H.; Lee, D. H.; Kim, Y. H.; Lee, Y. G.; Hahn, J. T. Bull. Korean Chem. Soc. 2006, 27, 1493. https://doi.org/10.5012/bkcs.2006.27.9.1493
  30. Georg, G. L.; He, P.; Kant, J.; Wu, Z. J. Org. Chem. 1993, 58, 5571. https://doi.org/10.1021/jo00073a001
  31. (a) Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521. https://doi.org/10.1016/S0040-4020(99)00845-5
  32. (b) Vogel, P. Curr. Org. Chem. 2000, 4, 455. https://doi.org/10.2174/1385272003376175
  33. Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. https://doi.org/10.1021/jo9804745