Synthesis of a new cerebroside isolated from Typhonium giganteum Engl

Chinese Journal of Chemistry

Volumn 21, Issue 7, 2003, Pages 937-943

  Xue Song, Chen ^a,b   Wu, Yu Lin ^a   Chen, Di Hua ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b INSTITUTE OF MEDICINAL PLANT DEVELOPMENT   (China)

Author keywords

Cerebroside; Chiron approach; Natural product; Synthesis; Typhonium giganteum Engl.

Indexed keywords

EID: 33748071151     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20030210743     Document Type: Article

References (36)

1. Tringal, C. Bioactive Compounds from Natural Sources, Taylor & Francis, 2001, p. 555.
2. (a) Munesada, K.; Yuasa, M.; Suga, T. J. Chem. Soc., Perkin Trans. 1 1991, 189.
3. (b) Natori, T.; Monta, M.; Akimoto, K.; Koezuka, Y. Tetrahedron 1994, 50, 2771.
4. (c) Irie, A.; Kubo, H.; Hoshi, M. J. Biochem. 1990, 107, 578.
5. (d) Kawai, G.; Ohbish, M.; Fujino, Y.; Ikeda, Y. J. Biol. Chem. 1986, 261, 779.
6. (e) Kang, S. S.; Kim, J. S.; Son, K. H.; Kim, H. P.; Chang, H. W. Chem. Pharm. Bull. 2001, 49, 321.
7. (f) Higuchi, R.; Jhou, J. X.; Inukai, K.; Komori, T. Liebigs Ann. Chem. 1991, 91, 745.
8. (a) Harouse, J. M.; Bhat, S.; Spitalnik, S. L.; Laughlin, M.; Stefano, K.; Silerberg, D. H.; Gronzalez-Scarano, F. Science 1991, 253, 320.
9. (b) Marchell, N. L.; Uchida, Y.; Brown, B. E.; Elias, P. M.; Holleran, W. M. J. Invest. Dermatol. 1998, 110, 383.
10. (c) Boldin, S.; Futerman, A. H. J. Neurochem. 1997, 68, 882.
11. (d) Schwarz, A.; Futerman, A. H. J. Neurosci. 1997, 17, 2929.
12. (e) Overmeire, I. V.; Boldin, S. A.; Dumont, F.; Calenbergh, S. V.; Siegers, G.; Keukeleire, D. D.; Futerman, A. H.; Herdewijn, P. J. Med. Chem. 1999, 42, 2697.
13. (a) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1990, 90, 1063.
14. (b) Graziani, A.; Passacantilli, P.; Oiancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921.
15. (c) Bär, T.; Schmidt, R. R. Liebigs Ann. Chem. 1988, 88, 669.
16. (d) Seki, M.; Kayo, A.; Mori, K. Tetrahrdron Lett. 2001, 42, 2357.
17. (e) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95.
18. (f) Akimoto, K.; Natori, T.; Morota, M. Tetrahedron Lett. 1993, 34, 5593.
19. (g) Natori, T.; Morita, M.; Akimoto, K.; Koezuka, Y. Tetrahedron 1994, 50, 2771.
20. (a) Arenz, C.; Giannis, A. Angew. Chem., Int. Ed. 2000, 39, 1440.
21. (b) Yokomatsu, T.; Takechi, H.; Akiyama, T.; Shibuya, S.; Kominato, T.; Soede, S.; Shimeno, H. Bioorg. Med. Chem. Lett. 2001, 11, 1277.
22. (c) Fantini, J.; Hammache, D.; Delezay, O. J. Biol. Chem. 1997, 272, 7245.
23. (d) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzalez-Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639.
24. (e) Carson, K. G.; Ganem, B.; Radin, N. S. Tetrahedron Lett. 1994, 35, 2659.
25. (f) Szulc, Z. M.; Hannun, Y. A.; Bielawska, A. Tetrahedron Lett. 2000, 41, 7821.
26. (a) Chen, X.-S.; Chen, D.-H.; Si, J.-Y.; Tu, G.-Z. J. Asian Nat. Prod. Res. 2001, 3, 277.
27. (b) Chen, X.-S.; Wu, Y.-L.; Chen, D.-H. Tetrahedron Lett. 2002, 43, 3529.
28. (a) Corey, E. J.; Choi, S. Tetrahedron Lett. 2000, 41, 2765.
29. (b) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1988, 88, 619.
30. (c) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191.
31. (d) He, L.; Byun, H. S.; Bittman, R. J. Org. Chem. 2000, 65, 7618.
32. Wang, X.-Z.; Wu, Y.-L.; Jiang, S.; Singh, G. J. Org. Chem. 2000, 65, 8146.
33. Tanaka, A.; Yamashita, K. Synthesis 1987, 570.
34. Wessel, H. P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin. Trans. 1 1985, 2247.
35. 4g
36. Deng, S. J.; Yu, B.; Xie, J. M.; Hui, Y. Z. J. Org. Chem. 1999, 64, 7265.