Regioselective Glycosylation of Neamine Core: A Facile Entry to Kanamycin B Related Analogues

Organic Letters

Volumn 6, Issue 4, 2004, Pages 585-588

  Chou, Chien Hung ^a   Wu, Chung Shieh ^a   Chen, Ching Hui ^a   Lu, Lung Dai ^b   Kulkarni, Suvarn S ^a   Wong, Chi Huey ^c   Hung, Shang Cheng ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^c GENOMICS RESEARCH CENTER   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE DERIVATIVE; KANAMYCIN B; NEAMINE; SUGAR;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION;

AMINOGLYCOSIDES; CATALYSIS; GLYCOSYLATION; INDICATORS AND REAGENTS; KANAMYCIN; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 1342332906     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0363927     Document Type: Article

References (32)

1. Aminoglycoside Antibiotics Umezawa, H., Hooper, I. H., Eds.: Springer-Verlag: New York, Heidelberg, 1982.
2. (a) Moazed, D.; Noller, H. F. Nature 1987, 327, 389-394.
3. (b) Woodcock, J.; Moazed, D.; Cannon, M.; Davies, J.; Noller, H. F. EMBO J. 1991, 10, 3099-3103.
4. (a) Fourmy, D.; Recht, M. I.; Blanchard, S. C.; Puglisi, J. D. Science 1996, 274, 1367-1371.
5. (b) Fourmy, D.; Yoshizawa, S.; Puglisi, J. D. J. Mol. Biol. 1998, 277, 333-345.
6. (c) Fourmy, D.; Recht, M. I.; Puglisi, J. D. J. Mol. Biol. 1998, 277, 347-362.
7. (d) Yoshizawa, S.; Fourmy, D.; Puglisi, J. D. EMBO J. 1998, 17, 6437-6448.
8. Kotra, L. P.; Mobashery, S. Curr. Org. Chem. 2001, 5, 193-205.
9. (a) Hermann, T.; Westhof, E. Curr. Opin. Biotechnol. 1998, 19, 66-73.
10. (b) Tor, Y. Angew. Chem., Int. Ed. 1999, 38, 1579-1582
11. . (c) Ecker, D. J.; Griffey, R. H. Drug Discov. Today 1999, 4, 420-429.
12. (d) Walter, F.; Vicens, Q.; Westhof, E. Curr. Opin. Chem. Biol. 1999, 3, 694-704.
13. (e) Hermann, T. Angew. Chem., Int. Ed. 2000, 39, 1890-1905.
14. (f) Sucheck, S. J.; Wong, C.-H. Curr. Opin. Chem. Biol. 2000, 4, 678-686.
15. Haddad, J.; Vakulenko, S.; Mobashery, S. J. Am. Chem. Soc. 1999, 121, 11922-11923 and references therein.
16. (a) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 10150-10155.
17. (b) Nunns, C. L.; Spence, L. A.; Slater, M. J.; Berrisford, D. J. Tetrahedron Lett. 1999, 40, 9341-9345.
18. (c) Ding, Y.; Swayze, E. E.; Hofstadler, S. A.; Griffey, R. H. Tetrahedron. Lett. 2000, 41, 4049-4052.
19. (a) Greenberg, W. A.; Priestley, E. S.; Sears, P. S.; Alper, P. B.; Rosenbohm, C.; Hendrix, M.; Hung, S.-C.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 6527-6541.
20. (b) Sucheck, S. J.; Wong, A. L.; Koeller, K. M.; Boehr, D. D.; Draker, K.; Sears, P.; Wright, G. D.; Wong, C.-H. J. Am. Chem. Soc. 2000, 122, 5230-5231.
21. (c) Sucheck, S. J.; Greenberg, W. A.; Tolbert, T. J.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1080-1084.
22. (a) Wang, J.; Li, J.; Tuttle, D.; Takemoto, J. Y.; Chang, C.-W. T. Org. Lett. 2002, 4, 3997-4000.
23. (b) Chang, C.-W. T.; Hui, Y.; Elchert, B.; Wang, J.; Li, J.; Rai, R. Org. Lett. 2002, 4, 4603-4606.
24. (c) Li, J.; Wang, J.; Hui, Y.; Chang, C.-W. T. Org. Lett. 2003, 5, 431-434.
25. Alper, P. B.; Hendrix, M.; Sears, P.; Wong, C.-H. J. Am. Chem. Soc. 1998, 120, 1965-1978.
26. Haddad, J.; Kotra, L. P.; Llano-Sotelo, B.; Kim, C.; Azucena, E. F., Jr. ; Liu, M.; Vakulenko, S. B.; Chow, C. S.; Mobashery, S. J. Am. Chem. Soc. 2002, 124, 3229-3237.
27. (a) Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
28. (b) Nyffeler, P. T.; Liang, C.-S.; Koeller, K. M.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 10773-10778.
29. (a) Hense, A.; Ley, S. V.; Osborn, H. M. I.; Owen, D. R.; Poisson, J.-F. ; Warriner, S. L.; Wesson, K. E. J. Chem. Soc., Perkin Trans. 1 1997, 2023-2031.
30. (b) Ley, S. V.; Baeschlin, D. K.; Dixon, D. J.; Foster, A. C.; Ince, S. J.; Priepke, H. W. M.; Reynolds, D. J. Chem. Rev. 2001, 101, 53-80.
31. In the BDA-protection of diol 1, although, the anomeric effect at the two acetal centers favored the formation of the isomer with anti-periplanar arrangement of OMe groups, the other isomer was also formed in minor proportion. This was not separated and the mixture was used as such for ensuing glycosylations. After the removal of BDA protecting group, individual products were obtained in pure form.
32. 1H COSY spectral analysis then established the correlation between all of the protons on each ring. The regioselectivity of glycosylation (O5 or O6) was determined by observation of the correlation with the OH protons in the COSY spectrum, wherever possible, and also judged from the multiplicity of H5 and H6 protons. NOESY spectral analysis was finally used to reaffirm the assignments. The α and β configurations were determined on the basis of coupling constant measurements of the respective anomeric protons (see the Supporting Information).