Cyclisation of meta-phenylene-bis-alanine derivatives

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

Andreas Ritzén and Torbjörn Frejd


Abstract

The cyclisation of a meta-phenylene-bis-alanine derivative with several different spacer moieties was investigated. A large difference in the ease of cyclisation was observed depending on which path of cyclisation was chosen. NMR studies indicate that the closed-loop molecules adopt folded conformations with the loop directly above the aromatic ring plane.


References

  1. A. V. R. Rao, M. K. Gurjar, K. L. Reddy and A. S. Rao, Chem. Rev., 1995, 95, 2135 CrossRef .
  2. U. Schmidt, A. Lieberknecht and J. Wild, Synthesis, 1988, 159 CrossRef CAS .
  3. I. Uchida, M. Ezaki, N. Shigematsu and M. Hashimoto, J. Org. Chem., 1985, 50, 1341 CrossRef CAS .
  4. R. Kannan and D. H. Williams, J. Org. Chem., 1987, 52, 5435 CrossRef .
  5. J. M. Humphrey and A. R. Chamberlin, Chem. Rev., 1997, 97, 2243 CrossRef CAS .
  6. J. H. Burckhalter and V. C. Stephens, J. Am. Chem. Soc., 1951, 73, 56 CrossRef CAS .
  7. W. von Ried and B. Schleimer, Liebigs Ann. Chem., 1961, 639, 68 Search PubMed .
  8. Y. Omote, Y. Fujinuma and N. Sugiyama, Bull. Chem. Soc. Jpn., 1969, 42, 1752 CAS .
  9. R. F. Chapman and G. A. Swan, J. Chem. Soc. (C), 1970, 865 RSC .
  10. R. Fitzi and D. Seebach, Tetrahedron, 1988, 44, 5277 CrossRef CAS .
  11. U. Schmidt, R. Meyer, V. Leitenberger and A. Lieberknecht, Angew. Chem., Int. Ed. Engl., 1989, 28, 929 Search PubMed .
  12. G. A. Brown and P. D. Edwards, Tetrahedron Lett., 1990, 31, 6581 CrossRef CAS .
  13. K. Undheim and M. Solbakken, PCT Int. Appl. WO 93/24522 PCT/GB93/01170 (Chem. Abstr., 1994, 121, 281231e) Search PubMed .
  14. A.-S. Carlström and T. Frejd, Synthesis, 1989, 414 CrossRef .
  15. A.-S. Carlström and T. Frejd, J. Org. Chem., 1990, 55, 4175 CrossRef .
  16. A.-S. Carlström and T. Frejd, J. Org. Chem., 1991, 56, 1289 CrossRef .
  17. A.-S. Carlström and T. Frejd, J. Chem. Soc., Chem. Commun., 1991, 1216 RSC .
  18. A.-S. Carlström and T. Frejd, Acta Chem. Scand., 1992, 46, 163 .
  19. B. Basu and T. Frejd, Acta Chem. Scand., 1996, 50, 316 CAS .
  20. B. Basu, S. K. Chattopadhyay, A. Ritzén and T. Frejd, Tetrahedron: Asymmetry, 1997, 8, 1841 CrossRef CAS .
  21. A. Ritzén, B. Basu, S. K. Chattopadhyay, F. Dossa and T. Frejd, Tetrahedron: Asymmetry, 1998, 9, 503 CrossRef CAS .
  22. J. M. Travins and F. A. Etzkorn, J. Org. Chem., 1997, 62, 8387 CrossRef CAS .
  23. M. J. Burk, J. E. Feaster, W. A. Nugent and R. L. Harlow, J. Am. Chem. Soc., 1993, 115, 10125 CrossRef CAS .
  24. U. Schmidt, A. Lieberknecht, U. Schanbacher, T. Beuttler and J. Wild, Angew. Chem., Int. Ed. Engl., 1982, 21, 770 Search PubMed .
  25. U. Schmidt, A. Lieberknecht and J. Wild, Synthesis, 1984, 53 CrossRef CAS .
  26. E. P. Prokof'ev and E. I. Karpeiskaya, Tetrahedron Lett., 1979, 737 CrossRef CAS .
  27. T. Shioiri, K. Ninomiya and S.-i. Yamada, J. Am. Chem. Soc., 1972, 94, 6203 CrossRef CAS .
  28. A. Ehrlich, H.-U. Heyne, R. Winter, M. Beyermann, H. Haber, L. A. Carpino and M. Bienert, J. Org. Chem., 1996, 61, 8831 CrossRef CAS .
  29. F. Cavelier-Frontin, G. Pèpe, J. Verducci, D. Siri and R. Jacquier, J. Am. Chem. Soc., 1992, 114, 8885 CrossRef CAS .
  30. M. Bodanszky and A. Bodanszky, The Practise of Peptide Synthesis, Springer-Verlag, Berlin, 1984 Search PubMed .
  31. S. Gladiali and L. Pinna, Tetrahedron: Asymmetry, 1991, 2, 623 CrossRef CAS .
  32. D. Marcovici-Mizrahi, H. E. Gottlieb, V. Marks and A. Nudelman, J. Org. Chem., 1996, 61, 8402 CrossRef CAS .
Click here to see how this site uses Cookies. View our privacy policy here.