A convenient route to imino sugars and analogues of siastatin B

Synlett

Volumn , Issue 15, 2004, Pages 2776-2778

  Birch, Nicola J ^a   Parsons, Phillip J ^a   Scopes, David I C ^b  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

^b UCB PHARMA   (Belgium)

Author keywords

Lactam; Dihydroxylation; Imino sugars; Ring closing metathesis; Siastatin B

Indexed keywords

BETA LACTAM; IMINOSUGAR; NATURAL PRODUCT; SIASTATIN B; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 10844258808     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-836021     Document Type: Article

References (26)

1. Chapleur, Y. Carbohydrate Mimics, Concepts and Methods; Wiley-VCH: Weinheim, 1998.
2. Asano, N. Curr. Top. Med. Chem. 2003, 3, 471.
3. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
4. Stutz, A. E. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond; Wiley-VCH: Weinheim, 1999.
5. Greimel, P.; Spreitz, J.; Stutz, A. E.; Wrodnigg, T. M. Curr. Top. Med. Chem. 2003, 3, 513.
6. Cox, T.; Lachmann, R.; Hollak, C.; Aerts, J.; van Weely, S.; Hrebicek, M.; Platt, F.; Butters, T.; Dwek, R.; Moyses, C.; Gow, I.; Elstein, D.; Zimran, A. The Lancet 2000, 355, 1481.
7. Butters, T. D.; Dwek, R. A.; Platt, F. M. Curr. Top. Med. Chem. 2003, 3, 561.
8. Umezawa, H.; Aoyagi, T.; Komiyama, T.; Morishima, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 1974, 27, 963.
9. Kawase, Y.; Takahashi, M.; Takatsu, T.; Arai, M.; Nakajima, M.; Tanzawa, K. J. Antibiot. 1996, 49, 61.
10. Mues, H.; Kazmaier, U. Synthesis 2001, 487.
11. For some recent examples see: (a) Batey, R. A.; Mackay, D. B. Tetrahedron Lett. 2000, 41, 9935.
12. (b) Scheuster, M.; He, W. F.; Blechert, S. Tetrahedron Lett. 2001, 42, 2289.
13. Cipolla, L.; La Ferla, B.; Nicotra, F. Curr. Top. Med. Chem. 2003, 3, 485.
14. McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565.
15. Pandey, G.; Kapur, M. Synthesis 2001, 1263.
16. Overkleeft, H. S.; Bruggeman, P.; Pandit, U. K. Tetrahedron 1998, 39, 3869.
17. Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971.
18. Amat, M.; Llor, N.; Hugert, M.; Molins, E.; Espinosa, E.; Bosen, J. Org. Lett. 2001, 3, 3257.
19. Ward, R. A.; Procter, G. Tetrahedron 1995, 57, 12301.
20. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
21. Alcaide, B.; Martincantalejo, Y.; Perezcastells, J.; Rodriguezlopez, J.; Sierra, A.; Monge, M. A.; Perezgarcia, V. J. Org. Chem. 1992, 57, 5921.
22. Banfi, L.; Cascio, G.; Ghiron, C.; Guanti, G.; Masghisi, E.; Narisano, E.; Riva, R. Tetrahedron 1994, 11983.
23. Tarling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans, 1 1999, 1695.
24. Bose, A. K.; Banik, B. K.; Mathur, C.; Wagle, D. R.; Manhas, M. S. Tetrahedron 2000, 56, 5603.
25. Murray, A. J.; Parsons, P. J.; Greenwood, E. S.; Viseux, E. M. E. Synthesis 2004, 1589.
26. 6SiNa: 414.2288; found: 414.2282.