Syntheses of optically active, unusual, and biologically important hydroxy-amino acids from d-glucosamine

Heterocycles

Volumn 43, Issue 1, 1996, Pages 11-14

  Shinozaki, Katsuo ^a,b   Mizuno, Kazuhiro ^a   Masaki, Yukio ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b ZERIA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001907935     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-7288     Document Type: Article

References (35)

1. S. Hunt, Chemistry and Biochemistry of the Amino Acids, ed by G. C. Barrett, Chapman and Hall, London, 1985, p.55; I. Wagner and H. Musso, Angew. Chem., Int. Ed. Engl., 1983, 22, 816.
2. S. Hunt, Chemistry and Biochemistry of the Amino Acids, ed by G. C. Barrett, Chapman and Hall, London, 1985, p.55; I. Wagner and H. Musso, Angew. Chem., Int. Ed. Engl., 1983, 22, 816.
3. Y. Ohfune, Acc. Chem. Res., 1992, 25, 360; J. Jurczak and A. Golebiowski, Chem. Rev., 1989, 89, 149; T. Yokomatsu, Y. Yuasa, and S. Shibuya, Heterocycles, 1992, 33, 1051.
4. Y. Ohfune, Acc. Chem. Res., 1992, 25, 360; J. Jurczak and A. Golebiowski, Chem. Rev., 1989, 89, 149; T. Yokomatsu, Y. Yuasa, and S. Shibuya, Heterocycles, 1992, 33, 1051.
5. Y. Ohfune, Acc. Chem. Res., 1992, 25, 360; J. Jurczak and A. Golebiowski, Chem. Rev., 1989, 89, 149; T. Yokomatsu, Y. Yuasa, and S. Shibuya, Heterocycles, 1992, 33, 1051.
6. W. L. Wolfrom, R. U. Lemieux, and S. Olin, J. Am. Chem. Soc., 1949, 71, 2780; M. Miyashita, N. Chida, and A. Yoshikoshi, J. Chem. Soc., Chem. Commun., 1982, 1354; S. M. Hecht, J. Am. Chem. Soc., 1979, 101, 3982; D. H. R. Barton, J. Org. Chem., 1989, 54, 3764; J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc., 1966, 1872, 1882; T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 1994, 35, 745 ; T. Sugawara and M. Narisada, Carbohyd. Res., 1989, 194, 125.
7. W. L. Wolfrom, R. U. Lemieux, and S. Olin, J. Am. Chem. Soc., 1949, 71, 2780; M. Miyashita, N. Chida, and A. Yoshikoshi, J. Chem. Soc., Chem. Commun., 1982, 1354; S. M. Hecht, J. Am. Chem. Soc., 1979, 101, 3982; D. H. R. Barton, J. Org. Chem., 1989, 54, 3764; J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc., 1966, 1872, 1882; T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 1994, 35, 745 ; T. Sugawara and M. Narisada, Carbohyd. Res., 1989, 194, 125.
8. W. L. Wolfrom, R. U. Lemieux, and S. Olin, J. Am. Chem. Soc., 1949, 71, 2780; M. Miyashita, N. Chida, and A. Yoshikoshi, J. Chem. Soc., Chem. Commun., 1982, 1354; S. M. Hecht, J. Am. Chem. Soc., 1979, 101, 3982; D. H. R. Barton, J. Org. Chem., 1989, 54, 3764; J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc., 1966, 1872, 1882; T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 1994, 35, 745 ; T. Sugawara and M. Narisada, Carbohyd. Res., 1989, 194, 125.
9. W. L. Wolfrom, R. U. Lemieux, and S. Olin, J. Am. Chem. Soc., 1949, 71, 2780; M. Miyashita, N. Chida, and A. Yoshikoshi, J. Chem. Soc., Chem. Commun., 1982, 1354; S. M. Hecht, J. Am. Chem. Soc., 1979, 101, 3982; D. H. R. Barton, J. Org. Chem., 1989, 54, 3764; J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc., 1966, 1872, 1882; T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 1994, 35, 745 ; T. Sugawara and M. Narisada, Carbohyd. Res., 1989, 194, 125.
10. W. L. Wolfrom, R. U. Lemieux, and S. Olin, J. Am. Chem. Soc., 1949, 71, 2780; M. Miyashita, N. Chida, and A. Yoshikoshi, J. Chem. Soc., Chem. Commun., 1982, 1354; S. M. Hecht, J. Am. Chem. Soc., 1979, 101, 3982; D. H. R. Barton, J. Org. Chem., 1989, 54, 3764; J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc., 1966, 1872, 1882; T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 1994, 35, 745 ; T. Sugawara and M. Narisada, Carbohyd. Res., 1989, 194, 125.
11. W. L. Wolfrom, R. U. Lemieux, and S. Olin, J. Am. Chem. Soc., 1949, 71, 2780; M. Miyashita, N. Chida, and A. Yoshikoshi, J. Chem. Soc., Chem. Commun., 1982, 1354; S. M. Hecht, J. Am. Chem. Soc., 1979, 101, 3982; D. H. R. Barton, J. Org. Chem., 1989, 54, 3764; J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc., 1966, 1872, 1882; T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 1994, 35, 745 ; T. Sugawara and M. Narisada, Carbohyd. Res., 1989, 194, 125.
12. W. L. Wolfrom, R. U. Lemieux, and S. Olin, J. Am. Chem. Soc., 1949, 71, 2780; M. Miyashita, N. Chida, and A. Yoshikoshi, J. Chem. Soc., Chem. Commun., 1982, 1354; S. M. Hecht, J. Am. Chem. Soc., 1979, 101, 3982; D. H. R. Barton, J. Org. Chem., 1989, 54, 3764; J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc., 1966, 1872, 1882; T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 1994, 35, 745 ; T. Sugawara and M. Narisada, Carbohyd. Res., 1989, 194, 125.
13. K. Shinozaki, K. Mizuno, H. Oda, and Y. Masaki, Chem. Lett., 1992, 2265.
14. (a) For isolation, structural study, and biological activity of AI-77-B, see: Y. Shimojima, H. Hayashi, T. Ooka, and M. Shibukawa, Tetrahedron, 1984, 40, 2519. : Y. Shimojima, T. Shirai, T. Baba, and H. Hayashi, J. Med. Chem., 1985, 28, 3 and references cited therein;
15. (a) For isolation, structural study, and biological activity of AI-77-B, see: Y. Shimojima, H. Hayashi, T. Ooka, and M. Shibukawa, Tetrahedron, 1984, 40, 2519. : Y. Shimojima, T. Shirai, T. Baba, and H. Hayashi, J. Med. Chem., 1985, 28, 3 and references cited therein;
16. (b) For total synthesis of AI-77-B, see: Y. Hamada, A. Kawai, Y. Kohno, O. Hara, and T, Shioiri, J. Am. Chem. Soc., 1989, 111, 1524; J-M. Drugnat and P. Vogel, Helv. Chim. Acta, 1993, 76, 222 and references cited therein.
17. (b) For total synthesis of AI-77-B, see: Y. Hamada, A. Kawai, Y. Kohno, O. Hara, and T, Shioiri, J. Am. Chem. Soc., 1989, 111, 1524; J-M. Drugnat and P. Vogel, Helv. Chim. Acta, 1993, 76, 222 and references cited therein.
18. (a) For isolation, structural study, and biological activity of calyculins, see: Y. Kato, N. Fusetani, S. Matsunaga, and K. Hashimoto, J. Am. Chem. Soc., 1986, 108, 2780; Y. Hamada, Y. Tanada, F. Yokokawa, and T. Shioiri, Tetrahedron Lett., 1991, 32, 5983 and references cited therein;
19. (a) For isolation, structural study, and biological activity of calyculins, see: Y. Kato, N. Fusetani, S. Matsunaga, and K. Hashimoto, J. Am. Chem. Soc., 1986, 108, 2780; Y. Hamada, Y. Tanada, F. Yokokawa, and T. Shioiri, Tetrahedron Lett., 1991, 32, 5983 and references cited therein;
20. (b) For total synthesis of antipodal (+)-calyculin A, see: D. A. Evans, J. R. Gage, and J. L. Leighton, J. Am. Chem. Soc., 1992, 114, 9438.
21. (a) S. Hanessian, R. Masse, and T. Nakagawa, Can. J. Chem., 1978, 56, 1509;
22. (b) R. W. Jeanloz, J. Am. Chem. Soc., 1957, 79, 2591; R. Gigg and C. D. Warren, J. Chem. Soc., 1965, 1351; P. H. Gross, K. Brendel, and H. K. Zimmerman, Liebigs Ann. Chem., 1965, 687, 175; K. Miyai, H. K. Zimmerman, and P. H. Gross, J. Org. Chem., 1969, 34, 1635.
23. (b) R. W. Jeanloz, J. Am. Chem. Soc., 1957, 79, 2591; R. Gigg and C. D. Warren, J. Chem. Soc., 1965, 1351; P. H. Gross, K. Brendel, and H. K. Zimmerman, Liebigs Ann. Chem., 1965, 687, 175; K. Miyai, H. K. Zimmerman, and P. H. Gross, J. Org. Chem., 1969, 34, 1635.
24. (b) R. W. Jeanloz, J. Am. Chem. Soc., 1957, 79, 2591; R. Gigg and C. D. Warren, J. Chem. Soc., 1965, 1351; P. H. Gross, K. Brendel, and H. K. Zimmerman, Liebigs Ann. Chem., 1965, 687, 175; K. Miyai, H. K. Zimmerman, and P. H. Gross, J. Org. Chem., 1969, 34, 1635.
25. (b) R. W. Jeanloz, J. Am. Chem. Soc., 1957, 79, 2591; R. Gigg and C. D. Warren, J. Chem. Soc., 1965, 1351; P. H. Gross, K. Brendel, and H. K. Zimmerman, Liebigs Ann. Chem., 1965, 687, 175; K. Miyai, H. K. Zimmerman, and P. H. Gross, J. Org. Chem., 1969, 34, 1635.
26. A. Klemer and H. Wilbers, Liebigs Ann. Chem., 1985, 2328.
27. 1H-nmr spectroscopy.
28. S. Hanessian, Carbohydr. Res., 1966, 2, 86.
29. w=0.050 for 1254 reflections.
30. B. Bernet and A. Vasella, Helv. Chim. Acta, 1984, 67, 1328.
31. For synthesis of the otically active hydroxyamino acid moieties of AI-77-B, see: A. Kawai, O. Hara, Y. Hamada, and T. Shioiri, Tetrahedron Lett., 1988, 29, 6331; H. Kotsuki, M. Iwasaki, and M. Ochi, Heterocycles, 1994, 38, 17 and references cited therein.
32. For synthesis of the otically active hydroxyamino acid moieties of AI-77-B, see: A. Kawai, O. Hara, Y. Hamada, and T. Shioiri, Tetrahedron Lett., 1988, 29, 6331; H. Kotsuki, M. Iwasaki, and M. Ochi, Heterocycles, 1994, 38, 17 and references cited therein.
33. For synthesis of the otically active natural hydroxyamino acid moieties of calyculins, see: (a) F. Yokokawa, Y. Hamada, and T. Shioiri, Synlett, 1992, 703 and references cited therein;
34. For antipodal hydroxyamino acid moieties, see: (b) Y. Hamada, Y. Tanada, F. Yokokawa, and T. Shioiri, Tetrahedron Lett., 1991, 32, 5983;
35. (c) A. B. Smith, III, B. A. Salvatore, K. G. Hull, and J. J-W. Duran, Tetrahedron Lett., 1991, 32, 4859.