An expedient asymmetric synthesis of a calystegine B4 analogue

Synthesis

Volumn , Issue 12, 2002, Pages 1707-1710

  Koulocheri, Sofia D ^a   Pitsinos, Emmanuel N ^b   Haroutounian, Serkos A ^a  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^b INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

Alkaloids; Asymmetric synthesis; Calystegines; Glycosidase inhibitors; Piperidines

Indexed keywords

HYDROXYLATION;

POLYHYDROXYLATION;

SYNTHESIS (CHEMICAL);

ALKALOID DERIVATIVE; CALYSTEGINE B4; GLYCOSIDASE INHIBITOR; TROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; TECHNIQUE;

EID: 0346037051     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-33706     Document Type: Article

References (27)

1. Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645.
2. For recent reviews on this subject see: (a) Zechel, D. L.; Withers, S. G. Acc. Chem. Res. 2000, 33, 11.
3. (b) Stütz, A. E. In Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond; Wiley-VCH: Weinheim, 1999.
4. (c) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750.
5. (a) Holman, R, R.; Cull, C. A.; Turner, R. C. Diabetes Care 1999, 22, 960.
6. (b) Platt, F. M.; Neises, G. R.; Reinkensmeir, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Science 1997, 276, 428.
7. Gross, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer Res. 1995, 1, 935.
8. (a) van den Broek, L. A. M. G. In Azasugars: Chemistry and their Biological Activity as Potential Anti-HIV Drugs, Carbohydrates in Drug Design; Witczak, Z. J.; Nieforth, K. A., Eds.; Marcel Dekker: New York, 1997, 471.
9. (b) Ratner, L.; Heyden, N. V.; Dedera, D. Virology 1991, 181, 180.
10. Some representative recent articles: (a) Liu, H.; Liang, X.; Søhoel, H.; Bülow, A.; Bols, M. J. Am. Chem. Soc. 2001, 123, 5116.
11. (b) Ghavami, A.; Johnston, B. D.; Jensen, M. T.; Svensson, B.; Pinto, B. M. J. Am. Chem. Soc. 2001, 123, 6268.
12. (c) Mao, H.; Joly, G. J.; Peeters, K.; Hoornaert, G. J.; Compernolle, F. Tetrahedron 2001, 57, 6955.
13. (d) Pandey, G.; Kapur, M. Tetrahedron Lett. 2000, 41, 8821.
14. (e) Enders, D.; Kirchhoff, J. H. Synthesis 2000, 2099.
15. (f) Herdeis, C.; Telser, J. Eur. J. Org. Chem. 1999, 1407.
16. (g) Herdeis, C.; Schiffer, T. Tetrahedron 1999, 55, 1043.
17. (h) For a comprehensive recent review on stereoselective synthesis of Prosopis and Cassia piperidine alkaloids see: Laschat, S.; Dickner, T. Synthesis 2000, 1781.
18. Tepfer, D.; Goldman, A.; Pamboukdjian, N.; Maille, M.; Lepingle, A.; Chevalier, D.; Denarie, J.; Rosenberg, C. J. Bacteriol. 1988, 170, 1153.
19. Molyneux, R. J.; Nash, R. J.; Asano, N. The Chemistry and Biological Activity of Calystegines and Related Nortropane Alkaloids, In Alkaloids: Chemical and Biological Perspectives, Vol. 11; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996, 303.
20. Nash, R. J.; Asano, N.; Watson, A. A. Polyhydroxylated Alkaloids that Inhibit Glycosidases, In Alkaloids: Chemical and Biological Perspectives, Vol. 11; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996, 346.
21. (a) Kato, A.; Adachi, I.; Miyauchi, M.; Ikeda, K.; Komae, T.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Wormald, M. R.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 1999, 316, 95.
22. (b) Asano, N.; Kato, A.; Oseki, K.; Kizu, H.; Matsui, K. Eur. J. Biochem. 1995, 229, 369.
23. Asano, N.; Kato, A.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. Carbohydr. Res. 1996, 293, 195.
24. Chapleur, Y. Carbohydrate Mimics, Concepts and Methods; Wiley-VCH: Weinheim, 1998.
25. García-Moreno, M. I.; Benito, J. M.; Mellet, C. O.; García Fernández, J. M. J. Org. Chem. 2001, 66, 7604.
26. Koulocheri, S. D.; Haroutounian, S. A. Synthesis 1999, 1889.
27. Ramsden, N. G.; Fleet, G. W. J.; Namgoong, S. K. J. Chem. Soc., Perkin Trans. 2 1991, 1991.