Synthesis of [60]fullerene-based α-amino acid derivatives

Tetrahedron

Volumn 61, Issue 6, 2005, Pages 1423-1431

  Enes, Roger F ^a   Tomé, Augusto C ^a   Cavaleiro, José A S ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

Alpha amino acids; Fullerenes; Ortho quinodimethanes; Pyrimidines

Indexed keywords

AMINO ACID DERIVATIVE; FULLERENE DERIVATIVE;

ADDITION REACTION; ARTICLE; MEMBRANE TRANSPORT; MOLECULAR MODEL; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SYNTHESIS;

BETULACEAE;

EID: 12344328451     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.12.007     Document Type: Article

References (30)

1. E. Nakamura, and H. Isobe Acc. Chem. Res. 36 2003 807 815
2. N. Tagmatarchis, and H. Shinohara Mini Rev. Med. Chem. 1 2001 339 348
3. T. da Ros, and M. Prato Chem. Commun. 1999 663 669
4. W. Jensen, S.R. Wilson, and D.I. Schuster Bioorg. Med. Chem. 4 1996 767 779
5. For an excellent review on the synthesis, properties and applications of fullerene-based amino acids and peptides, see A. Bianco, T. da Ross, M. Prato, and C. Toniolo J. Pept. Sci. 7 2001 208 219
6. G. Jung, T. Redemann, K. Kroll, S. Meder, A. Hirsch, and G. Boheim J. Pept. Sci. 9 2003 784 798
7. P. Sofou, Y. Elemes, E. Panou-Pomonis, A. Stavrakoudis, V. Tsikaris, C. Sakarellos, M. Sakarellos-Daitsiotis, M. Maggini, F. Formaggio, and C. Toniolo Tetrahedron 60 2004 2823 2828
8. B. Illescas, J. Rifé, R.M. Ortuño, and N. Martín J. Org. Chem. 65 2000 6242 6248
9. F. Pellarini, D. Pantarotto, T. da Ros, A. Giangaspero, A. Tossi, and M. Prato Org. Lett. 3 2001 1848 1854
10. D. Pantarotto, A. Bianco, F. Pellarini, A. Tossi, A. Giangaspero, I. Zelezetsky, J.-P. Briand, and M. Prato J. Am. Chem. Soc. 124 2002 12543 12549
11. A. Bianco, D. Pantarotto, J. Hoebeke, J.-P. Briand, and M. Prato Org. Biomol. Chem. 1 2003 4141 4143
12. G.A. Burley, P.A. Keller, S.G. Pyne, and G.E. Ball J. Org. Chem. 67 2002 8316 8330
13. S. Kotha, and A.K. Ghosh Tetrahedron Lett. 45 2004 2931 2934
14. A.C. Tomé, R.F. Enes, J.P.C. Tomé, J. Rocha, M.G.P.M.S. Neves, J.A.S. Cavaleiro, and J. Elguero Tetrahedron 54 1998 11141 11150
15. Fullero[1,2-g]quinazoline derivatives were also prepared by a similar procedure but using cyclobutapyrimidines as precursors of the pyrimidine ortho-quinodimethanes. B. González, A. Herrera, B. Illescas, N. Martín, R. Martínez, F. Moreno, L. Sánchez, and A. Sánchez J. Org. Chem. 63 1998 6807 6813
16. J.-M. Janot, E. Bienvenüe, P. Seta, R.V. Bensasson, A.C. Tomé, R.F. Enes, J.A.S. Cavaleiro, S. Leach, X. Camps, and A. Hirsch J. Chem. Soc., Perkin Trans. 2 2000 301 306
17. A.C. Tomé, J.A.S. Cavaleiro, and R.C. Storr Tetrahedron 52 1996 1735 1746
18. To prevent the photo-oxidation of adduct 5c to sulfoxide or sulfone, it was protected from light during purification; it was then stored in the fridge.
19. M. Ohno, N. Koide, H. Sato, and S. Eguchi Tetrahedron 53 1997 9075 9086
20. D.H. Williams, and I. Fleming Spectroscopic Methods In Organic Chemistry 4th ed. Revised 1989 McGraw-Hill London p. 47-51
21. A. Hirsch, I. Lamparth, and H.R. Karfunkel Angew. Chem., Int. Ed. Engl. 33 1994 437 438
22. M. Taki, S. Sugita, Y. Nakamura, E. Yashima, Y. Okanoto, and J. Nishimura J. Am. Chem. Soc. 119 1997 926 932
23. Y. Nakamura, M. Taki, S. Tobita, H. Shizuka, H. Yokoi, K. Ishiguro, Y. Sawaki, and J. Nishimura J. Chem. Soc., Perkin Trans. 2 1999 127 130
24. T. Ishi-i, K. Nakashima, S. Shinkai, and A. Ikeda J. Org. Chem. 64 1999 984 990
25. T. Ishi-i, and S. Shinkai Tetrahedron 55 1999 12515 12530
26. Y. Nakamura, A. Asami, S. Inokuma, T. Ogawa, M. Kikuyama, and J. Nishimura Tetrahedron Lett. 41 2000 2193 2197
27. Q. Lu, D.I. Schuster, and S.R. Wilson J. Org. Chem. 61 1996 4764 4768
28. L. Isaacs, R.F. Haldimann, and F. Diederich Angew. Chem., Int. Ed. Engl. 33 1994 2339 2342
29. Y. Rubin, S. Khan, D.I. Freedberg, and C.Z. Yeretzian J. Am. Chem. Soc. 115 1993 344 345
30. T. Tago, T. Minowa, Y. Okada, and J. Nishimura Tetrahedron Lett. 34 1993 8461 8464