View PDF Version
 
DOI: 10.1039/CS9972600377 (Review Article) Reference Section for: Chem. Soc. Rev., 1997, 26, 377-386

Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method

(Note: The full text of this document is currently only available in the PDF Version )

Iwao Ojima and Francette Delaloge

Abstract

Recent advances in the syntheses of enantiopure synthetic building blocks useful for non-protein amino acids, dipeptides, oligopeptides using solid state peptide synthesis, isoserines (norstatines), dipeptide isosteres [hydroxy(keto)ethylene, hydroxyethylamine, hydroxyethylene and dihydroxyethylene isosteres], taxoids, polyamines, poly(amino alcohol)s and poly(amino ether)s, and other biologically active compounds through applications of the β-lactam Synthon method is reviewed.

References

  1. G. I. Georg, The Organic Chemistry of β-Lactams, VCH, New York, 1992, and references cited therein. Search PubMed.
  2. I. Ojima, Acc. Chem. Res., 1995, 28, 383 Search PubMed.
  3. I. Ojima, in Advances in asymmetric synthesis, J. P. Inc., New York, 1995, vol. 1, pp. 95–146. Search PubMed.
  4. G. I. Georg and V. T. Ravikumar, in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH Publishers, New York, 1992; p. 295. Search PubMed.
  5. J. Aszodi, A. Bonnet and G. Teusch, Tetrahedron, 1990, 46, 1579 Search PubMed.
  6. G. I. Georg and Z. Wu, Tetrahedron Lett., 1994, 35, 381 Search PubMed.
  7. Y. Hashimoto, A. Kai and K. Saigo, Tetrahedron Lett., 1995, 36, 8821 Search PubMed.
  8. A. K. Bose, M. S. Manhas, J. M. V. D. Veen, S. S. Bari and D. R. Wagle, Tetrahedron, 1992, 48, 4831 Search PubMed.
  9. I. Ojima, K. Nakahashi, S. M. Brandstadter and N. Hatanaka, J. Am. Chem. Soc., 1987, 109, 1798 Search PubMed.
  10. M. Jayaraman, A. R. Deshmukh and B. M. Bhawal, Tetrahedron, 1996, 52, 8989 Search PubMed.
  11. N. Ikota and A. Hanaki, Heterocycles, 1984, 22, 2227 Search PubMed.
  12. R. D. G. Cooper, B. W. Daughery and D. B. Boyd, Pure Appl. Chem., 1987, 59, 485 Search PubMed.
  13. D. A. Evans and E. B. Sjogren, Tetrahedron Lett., 1985, 26, 3783 Search PubMed.
  14. C. Palomo, J. M. Aizpurua, M. Legido, R. Galarza, P. M. Deya, J. Dunogués, J. P. Picard, A. Ricci and G. Seconi, Angew. Chem., Int. Ed. Engl., 1996, 35, 1239 Search PubMed.
  15. I. Ojima, S. D. Kuduk, J. C. Slater, R. H. Gimi and C. M. Sun, Tetrahedron, 1996, 52, 209 Search PubMed.
  16. I. Ojima, S. D. Kuduk, P. P. Pera, J. M. Veith and R. J. Bernacki, J. Med. Chem., 1997, 40, 279 Search PubMed.
  17. I. Ojima, J. C. Slater, P. P. Pera, J. M. Veith, A. Abouabdellah, J.-P. Bégué and R. J. Bernacki, Bioorg. Med. Chem. Lett., 1997, 7, 133 Search PubMed.
  18. I. Ojima, J. C. Slater, E. Michaud, S. D. Kuduk, P.-Y. Bounaud, P. Vrignaud, M.-C. Bissery, J. Veith, P. Pera and R. J. Bernacki, J. Med. Chem., 1996, 39, 3889 Search PubMed.
  19. I. Ojima, J. C. Slater, S. D. Kuduk, C. S. Takeuchi, R. H. Gimi, C.-M. Sun, Y. H. Park, P. Pera, J. M. Veith and R. J. Bernacki, J. Med. Chem., 1997, 40, 267 Search PubMed.
  20. R. A. Holton, R. J. Biediger and P. D. Boatman, in Taxol: Science and Applications, ed. M. Suffness, CRC Press, New York, 1995, pp. 97–121. Search PubMed.
  21. M. J. Jung, in Chemistry and Biochemistry of Amino Acids, ed. G. C. Barrett, Chapman and Hall, New York, 1985, p. 227. Search PubMed.
  22. S. Thaisrivongs, D. T. Pals, L. T. Kroll, S. R. Turner and F.-S. Han, J. Med. Chem., 1987, 30, 976 Search PubMed.
  23. J. R. Huff, J. Med. Chem., 1991, 34, 2305 Search PubMed.
  24. Taxane Anticancer Agents: Basic Science and Current Status, ed. G. I. Georg, T. T. Chen, I. Ojima, and D. M. Vyas, ACS, Washington DC, 1995. Search PubMed.
  25. M. Suffness, Taxol: Science and Applications, CRC Press, New York, 1995. Search PubMed.
  26. Y. Kobayashi, Y. Takemoto, T. Kamijo, H. Harada, Y. Ito and S. Terashima, Tetrahedron, 1992, 48, 1853 Search PubMed.
  27. E. W. Ng, Dissertation, State University of New York at Stony Brook, 1996..
  28. C. Palomo, J. M. Aizpurua, J. M. Garcia, M. Iturburu and J. M. Odriozola, J. Org. Chem., 1994, 59, 5184 Search PubMed.
  29. D. M. Spero, S. Kapadia and V. Farina, Tetrahedron Lett., 1995, 36, 4543 Search PubMed.
  30. I. Ojima, E. W. Ng and C. M. Sun, Tetrahedron Lett., 1995, 36, 4547 Search PubMed.
  31. I. Ojima, H. Wang, T. Wang and E. Ng, 217th American Chemical Society National Meeting, San Francisco, April 13–17, 1997: Abstr., ORGEN 52. Search PubMed.
  32. P.-J. Colson and L. S. Hegedus, J. Org. Chem., 1993, 58, 5918 Search PubMed.
  33. T. Wang, F. Delaloge and I. Ojima, 218th American Chemical Society National Meeting, Las Vegas, September 7–11, 1997: Abstr., ORGN 210. Search PubMed.
  34. J. Kant, W. S. Schwartz, C. Fairchild, Q. Gao, S. Huang, B. H. Long, J. F. Kadow, V. Farina and D. Vyas, Tetrahedron Lett., 1996, 37, 6495 Search PubMed.
  35. I. Ojima, M. Zhao, T. Yamato, K. Nakahashi, M. Yamashita and R. Abe, J. Org. Chem., 1991, 56, 5263 Search PubMed.