Scale-up synthesis of swainsonine: A potent #-mannosidase II inhibitor

Organic Process Research and Development

Volumn 12, Issue 5, 2008, Pages 831-836

  Sharma, Pradeep K ^a   Shah, Rajan N ^a   Carver, Jeremy P ^a  

^a GLYCO Design Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58149141780     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op800059y     Document Type: Article

References (41)

1. (a) For selected reviews see: deMelo, E. B.; de Silveria Gomes, A.; Carvalho, I. Tetrahedron 2006, 62, 10277.
2. (b) Lillelund, V. H.; Jensen, H. H.; Liang, X. F.; Bols, M. Chem. Rev. 2002, 102, 515.
3. (c) Heihtman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750.
4. (d) deMelo, E. B.; de Silveria Gomes, A.; Carvalho, I. Tetrahedron 2006, 62, 10277.
5. (a) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645.
6. (b) Asano, N. Glycobiology 2003, 13, 93R.
7. (c) Watson, A.; Fleet, G. W. J.; Asano, N.; Molyneux, R. J.; Nash, R. J. Photochemistry 2001, 56, 265.
8. (d) Gerber-Lemaire, S.; Juillerat-Jeanneret, L. Mini-Rev. Med.Chem. 2006, 6, 1043.
9. (a) Colegate, S. M.; Dorling, P. R.; Huxtable, C. R. Aust. J. Chem. 1979, 32, 2257.
10. (b) Molyneux, R. J.; James, L. F. Science (Washington, D.C.) 1982, 216, 190.
11. (c) Davis, D.; Schwarz, P.; Hernandez, T.; Mitchell, M.; Warnock, B.; Elbein, A. D. Plant Physiol. 1984, 76, 972.
12. (d) Skelton, B. W.; White, A. H. Aust. J. Chem. 1980, 33, 435.
13. (a) Taylor, P. C.; Winchester, B. G. lminosugars as Glycosidase Inhibitors 1999, 125.
14. (b) Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045.
15. (c) Fellow, L. E.; Kite. G. C.: Nash, R. J.; Simmonds, M. S. J.; Scofield, A. M. Rec. Adv. Phytochem. 1989, 23, 395.
16. (d) Goss, P. E.; Reid, C. L.; Bailey, D.; Dennis, J. W. Clin. Cancer Res. 1997, 3, 11077.
17. (e) Elbein, A. D. FASEB J. 1991, J. 3055.
18. (f) Galustian, C.; Foulds, S.; Dye, J. F.; Guillou, P. J. Immunopharmacology 1994, 27, 165.
19. (g) Grzegorzewski, K.; Newton, S. A.; Akiyama, S. K.; Sharrow, S.; Olden, K.; White, S. L. Cancer Commun. 1989, 1, 373.
20. (h) Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
21. (i) Di Bello Cenci, I.; Fleet, G.; Tadano, S. K.; Winchester, B. Biochem. J. 1989, 259, 855.
22. (a) Nemr, A. E. Tetrahedron 2000, 56, 8579.
23. (b) Martin, R.; Murruzzu, C. A; Riera, M. A. J. Org. Chem. 2005, 70, 2325, and references cited there-in.
24. (c) Heimgaertner, G.; Raatz, D.; Reiser, O. Tetrahedron 2005, 61, 643.
25. (d) Pearson, W. H.; Ren, Y.; Powers, J. D. Heterocycles 2002, 58, 421.
26. (e) Lindsay, K. B.; Pyne, S. G. Aust. J. Chem. 2004, 57, 669.
27. (f) Guo, H.; O'Doherty, G. A. Org. Lett. 2006, 8, 1609.
28. Bennett, R. B.; Choi, J. R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580.
29. Hiskey, M. A. Chem. Eng. News 2005, 83 (30), 5.
30. (a) Mitsunobu, O.; Yamada, Y. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
31. (b) Mitsunobu, O. Synthesis 1981, 1.
32. (c) Castro, B. R. Org. React. 1983, 29, 1.
33. (d) Hughes, D. L. Org. Prep. 1990, 28, 127.
34. (e) Loibner, H.; Zbiral, E. Helv. Chim. Acta 1977, 60, 417.
35. (f) Chen, C. P.; Prasad, K.; Repic, O. Tetrahedron Lett. 1991, 32, 7175.
36. He, L.; Wanunu, M.; Byun, H.; Bittman, R. J. Org. Chem. 1999, 64, 6049.
37. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
38. (a) Borowitz, I. J.; Williams, G. J. J. Org. Chem. 1967, 32, 4157.
39. (b) Lewis, J.; Pearce, A. A. J. Chem. Soc. B 1969, 863.
40. (c) Barieux, J. J.; Gore, J. Tetrahedron 1972, 28, 1555.
41. U.S. Patent Publication No. US2003105326 A1; U.S. Patent Publication No. US20040063951 A1.