A new approach to 1-deoxy-azasugars: Asymmetric synthesis of 1-deoxymannojirimycin and 1-deoxyaltronojirimycin

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 5, 1997, Pages 741-746

  Xu, Yi Ming ^a   Zhou, Wei Shan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748723128     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a605128f     Document Type: Article

References (26)

1. L. E. Fellows, E. A. Bell, D. G. Lynn, F. J. Pilkiewicz, I. Miura and K. Nakanishi, J. Chem. Soc., Chem. Commun., 1979, 977.
2. (a) G. Legler, E. Julich, Carbohydr. Res., 1984, 128, 61;
3. (b) U. Fuhrmann, E. Bause, G. Legler and H. Ploegh, Nature, 1984, 307, 755.
4. S. V. Evans, L. E. Fellows, T. K. M. Shing and G. W. J. Fleet, Phytochemistry, 1985, 24, 1953.
5. M. Yagi, T. Kouno, Y. Aoyagi and H. Murai, Nippon Nogeikagaku Kaishi, 1976, 50, 571
6. (Chem. Abstr., 86, 167851r).
7. (a) S. Murso and S. Miyata, Agric. Biol. Chem., 1980, 44, 219;
8. (b) U. Fuhrmann, E. Bause and H. Ploegh, Biochim. Biophys. Acta, 1985, 825, 95;
9. (c) A. M. Scofield, L. E. Fellows, R. J. Nash and G. W. J. Fleet, Life Sci., 1986, 39, 645.
10. (a) G. C. Look, C. H. Fotsch and C. H. Wong, Acc. Chem. Res., 1993, 26, 182;
11. (b) G. R. Cook, L. G. Beholz and J. R. Stille, J. Org. Chem., 1994, 59, 3575 and references cited therein.
12. (a) A. B. Hughes and A. J. Rudge, Natural Product Reports, 1994, 135;
13. (b) R. H. Furneaux, P. C. Tyler and L. A. Whitehouse, Tetrahedron Lett., 1993, 34, 3613 and several references cited therein.
14. H. J. Altenbach and K. Himmeldirk, Tetrahedron Asymmetry, 1995, 6, 1077.
15. (a) W. S. Zhou, Z. H. Lu and Z. M. Wang, Tetrahedron Lett., 1991, 32, 1467;
16. (b) W. S. Zhou, Z. H. Lu and Z. M. Wang, Tetrahedron, 1993, 49, 2641.
17. (a) Z. H. Lu and W. S. Zhou, J. Chem. Soc., Perkin Trans. 1, 1993, 593;
18. (b) Z. H. Lu and W. S. Zhou, Tetrahedron, 1993, 49, 4659;
19. (c) W. S. Zhou, W. G. Xie, Z. H. Lu and X. F. Pan, Tetrahedron Lett., 1995, 36, 1291.
20. Preliminary communication see Y. M. Xu and W. S. Zhou, Tetrahedron Lett., 1996, 37, 1461.
21. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768.
22. G. W. J. Fleet and P. W. Smith, Tetrahedron Lett., 1985, 26, 1469.
23. K. H. Park, Y. J. Yoon and S. G. Lee, J. Chem. Soc., Perkin Trans. 1, 1994, 2621.
24. Y. Gao and K. B. Sharpless, J. Am. Chem. Soc., 1988, 110, 7538.
25. T. Shono, Y. Matsumura, K. Tsubata and K. Uchida, J. Org. Chem., 1986, 51, 2590.
26. E. J. Corey and T. M. Eckrich, Tetrahedron Lett., 1983, 24, 3163.