An Efficient, Fully Stereocontrolled Total Synthesis of N-Benzoyl-L-daunosamine

Journal of Organic Chemistry

Volumn 51, Issue 22, 1986, Pages 4245-4249

  Iida, Hideo ^a   Yamazaki, Naoki ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; N BENZOYLDAUNOSAMINE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; THEORETICAL STUDY;

EID: 0023005852     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00372a026     Document Type: Article

References (47)

1. Arcamone, F.; Cassinelli, G.; Orzezzi, P.; Franceschi, G.; Mondelli, R. J. Am. Chem. Soc. 1964, 86, 5335.
2. Wong, C. M.; Ho, T.-L.; Niemczura, W. P. Can. J. Chem. 1975, 53, 3144.
3. Dyong, I.; Wiemann, R. Angew. Chem., Int. Ed. Engl. 1978, 17, 682.
4. Iwataki, I.; Nakamura, Y.; Takahashi, K.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1979, 52, 2731.
5. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1981, 46, 227.
6. DeShong, P.; Leginus, J. M. J. Am. Chem. Soc. 1983, 105, 1686.
7. DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598.
8. Danishefsky, S. J.; Maring, C. J. J. Am. Chem. Soc. 1985, 107, 1269.
9. Sammes, P. G.; Thetford, D. J. Chem. Soc., Chem. Commun. 1985, 352.
10. Hirama, M.; Shigemoto, T.; Ito, S. Tetrahedron Lett. 1985, 26, 4137.
11. Warm, A.; Vogel, P. Tetrahedron Lett. 1985, 26, 5127.
12. Hauser, F. M.; Ellen-berger, S. R. J. Org. Chem. 1986, 51, 50.
13. Richardson, A. C. J. Chem. Soc. D. 1965, 627.
14. Richardson, A. C. Carbohydr. Res. 1967, 4, 422.
15. Baer, H. H.; Capek, K.; Cook, M. C. Can. J. Chem. 1969, 47, 89.
16. Marsh, J. P.; Mosher, C. W.; Acton, E. M.; Goodman, L. J. Chem. Soc. D. 1967, 973.
17. Horton, D.; Weckerle, W. Carbohydr. Res. 1975, 44, 227.
18. Yamaguchi, T.; Kojima, M. Carbohydr. Res. 1977, 59, 343.
19. Pauls, H. W.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1983, 1031.
20. Grethe, G.; Mitt, T.; Williams, T. H.; Uskokovic, M. R. J. Org. Chem. 1983, 48, 5309.
21. Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Org. Chem. 1984, 49, 3951.
22. Fronza, G.; Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1980, 442.
23. Dyong, I.; Wiemann, R. Chem. Ber. 1980, 113, 2666.
24. Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 4017.
25. Wovkulich, P. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1981, 103, 3956.
26. Dyong, I.; Friege, H.; zu Hone, T. Chem. Ber. 1982, 115, 256.
27. Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Org. Chem. 1983, 48, 909.
28. Grethe, G.; Sereno, J.; Williams, T. H.; Uskokovic, M. R. J. Org. Chem. 1983, 48, 5315.
29. Mukaiyama, T. Goto, Y.; Shoda, S. Chem. Lett. 1983, 671.
30. Hauser, F. M.; Rhee, R. P.; Ellen-berger, S. R. J. Org. Chem. 1984, 49, 2236.
31. Hiyama, T.; Nishide, K.; Kobayashi, K. Chem. Lett. 1984, 361.
32. Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5409.
33. Iida, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 1985, 26, 3255.
34. Iida, H. Yamazaki. N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069.
35. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
36. Forbes, C. P.; Wenteler, G. L.; Wiechers, A. J. Chem. Soc., Perkin Trans. 1 1977, 2353.
37. Abbott, R. E.; Spencer, T. A. J. Org. Chem. 1980, 45, 5398.
38. Bal, S. A.; Marfat, A.; Helquist, P. J. Org. Chem. 1982, 47, 5045.
39. Paquette, L. A.; Leone-Bay, A. J. Am. Chem. Soc. 1983, 105, 7352.
40. Still, W. C.; McDonald, J. H., III. Tetrahedron Lett. 1980, 21, 1031.
41. Still, W. C.; Schneider, J. A. Tetrahedron Lett. 1980, 21, 1035
42. Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 3769.
43. McGarvey, G. J.; Kimura, M. J. Org. Chem. 1982, 47, 5420.
44. Kelly, T. R.; Kaul, P. N. J. Org. Chem. 1983, 48, 2775.
45. Fronza, G.; Fuganti, C.; Grasselli, P. J. Chem. Soc., Perkin Trans. 1 1982, 885.
46. Guindon, Y.; Yoakim, C.; Morton, H. E. J. Org. Chem. 1984, 49, 3912.
47. Fuji, K.; Ichikawa, K.; Node, M.; Fujita, E. J. Org. Chem. 1979, 44, 1661.