New entry for asymmetric deoxyazasugar synthesis: Syntheses of deoxymannojirimycin, deoxyaltrojirimycin and deoxygalactostatin

Chemical Communications

Volumn , Issue 1, 1999, Pages 41-42

  Asano, Koji ^a   Hakogi, Toshikazu ^a   Iwama, Seiji ^a   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYMANNONOJIRIMYCIN; 4 METHOXYCARBONYLOXAZOLIDINONE; DEOXYALTROJIRIMYCIN; DEOXYGALACTOSTATIN; OXAZOLIDINONE DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033531159     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807532h     Document Type: Article

References (16)

1. E. W. Baxter and A. B. Reitz, J. Org. Chem., 1994, 59, 3175; F. M. Platt, G. R. Neises, R. A. Dwek and T. D. Butters, J. Biol. Chem., 1994, 269, 8362 and references cited therein.
2. E. W. Baxter and A. B. Reitz, J. Org. Chem., 1994, 59, 3175; F. M. Platt, G. R. Neises, R. A. Dwek and T. D. Butters, J. Biol. Chem., 1994, 269, 8362 and references cited therein.
3. L. E. Fellows, E. A. Bell, D. G. Lynn, F. J. Pilkiewcz, I. Miura and K. Nakanishi, J. Chem. Soc., Chem. Commun., 1979, 977.
4. (a) X. Yi-Ming and Z. Wei-Shan, J. Chem. Soc., Perkin Trans. 1, 1997, 741;
5. (b) R. Grandel and U. Kazmaier, Tetrahedron Lett., 1997, 38, 8009.
6. Y. Miyake and M. Ebata, J. Antibiol., 1987, 40, 122; Y. Miyake and M. Ebata, Agric. Biol. Chem., 1988, 52, 153.
7. Y. Miyake and M. Ebata, J. Antibiol., 1987, 40, 122; Y. Miyake and M. Ebata, Agric. Biol. Chem., 1988, 52, 153.
8. Deoxymannojirimycin: (a) K. H. Yong, Y. J. Yoon and S. G. Lee, J. Chem. Soc., Perkin Trans. 1, 1994, 2621;
9. (b) X.-D. Wu, S.-K. Khim, X. Zhang, E. M. Cederstrom and P. S. Mariano, J. Org. Chem., 1998, 63, 841 and references cited therein. Deoxyaltrojirimycin: see ref. 3. Deoxygalactostatin:
10. (c) P. L. Barili, G. Berti, G. Catelani, F. D'Andrea, F. D. Rensis and L. Puccioni, Tetrahedron, 1997, 53, 3407;
11. (d) J. P. Shilvock and G. W. J. Fleet, Synlett, 1998, 554 and references cited therein.
12. S. Katsumura, N. Yamamoto, M. Morita and Q. Han, Tetrahedron: Asymmetry, 1994, 5, 161 and references cited therein.
13. S. Katsumura, Y. Yamamoto, E. Fukuda and S. Iwama, Chem. Lett., 1995, 393; M. Murakami, S. Iwama, S. Fujii, K. Ikeda and S. Katsumura, Bioorg. Med. Chem. Lett., 1997, 7, 1725.
14. S. Katsumura, Y. Yamamoto, E. Fukuda and S. Iwama, Chem. Lett., 1995, 393; M. Murakami, S. Iwama, S. Fujii, K. Ikeda and S. Katsumura, Bioorg. Med. Chem. Lett., 1997, 7, 1725.
15. S. Iguchi, H. Nakai, M. Hayashi and H. Yamamoto, J. Org. Chem., 1979, 44, 1363.
16. S. J. Danishefsky, D. M. Armistead, F. E. Wincott, H. G. Selnick and R. Hungate, J. Am. Chem. Soc., 1989, 111, 2967.