Dihydroxypyrrolidines C-linked to galactose. Total synthesis of a specific inhibitor of α-mannosidases

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 7, 1997, Pages 893-896

  Kraehenbuehl, Karin ^a   Picasso, Sylviane ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA MANNOSIDASE; DISACCHARIDE; GLYCOSIDASE INHIBITOR;

ARTICLE; BEAN; CHIRALITY; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030944423     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00135-2     Document Type: Article

References (44)

1. See e.g.: Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131; Rademacher, T.W.; Parekh, R.B.; Dwek, R.A. Annu. Rev. Biochem. 1988, 57, 785; Rice, G.E.; Bevilacqua, M.P. Science 1989, 246, 1303; Smith, C.A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M.P.; Jerzy, R.; Dower, S.K.; Cosman, D.; Goodwin, R.G. Science 1990, 248, 1019; Stütz, A.E. Angew. Chem. Int. Ed. Engl. 1996, 35, 1926.
2. See e.g.: Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131; Rademacher, T.W.; Parekh, R.B.; Dwek, R.A. Annu. Rev. Biochem. 1988, 57, 785; Rice, G.E.; Bevilacqua, M.P. Science 1989, 246, 1303; Smith, C.A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M.P.; Jerzy, R.; Dower, S.K.; Cosman, D.; Goodwin, R.G. Science 1990, 248, 1019; Stütz, A.E. Angew. Chem. Int. Ed. Engl. 1996, 35, 1926.
3. See e.g.: Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131; Rademacher, T.W.; Parekh, R.B.; Dwek, R.A. Annu. Rev. Biochem. 1988, 57, 785; Rice, G.E.; Bevilacqua, M.P. Science 1989, 246, 1303; Smith, C.A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M.P.; Jerzy, R.; Dower, S.K.; Cosman, D.; Goodwin, R.G. Science 1990, 248, 1019; Stütz, A.E. Angew. Chem. Int. Ed. Engl. 1996, 35, 1926.
4. See e.g.: Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131; Rademacher, T.W.; Parekh, R.B.; Dwek, R.A. Annu. Rev. Biochem. 1988, 57, 785; Rice, G.E.; Bevilacqua, M.P. Science 1989, 246, 1303; Smith, C.A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M.P.; Jerzy, R.; Dower, S.K.; Cosman, D.; Goodwin, R.G. Science 1990, 248, 1019; Stütz, A.E. Angew. Chem. Int. Ed. Engl. 1996, 35, 1926.
5. See e.g.: Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131; Rademacher, T.W.; Parekh, R.B.; Dwek, R.A. Annu. Rev. Biochem. 1988, 57, 785; Rice, G.E.; Bevilacqua, M.P. Science 1989, 246, 1303; Smith, C.A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M.P.; Jerzy, R.; Dower, S.K.; Cosman, D.; Goodwin, R.G. Science 1990, 248, 1019; Stütz, A.E. Angew. Chem. Int. Ed. Engl. 1996, 35, 1926.
6. Ganem, B. Acc. Chem. Res. 1996, 29, 340 and ref. cited therein; van den Broek, L.A.G.M.; Vermaas, D.J.; Heskamp, B.M.; van Boeckel, C.A.A.; Tan, M.C.A.A.; Bolscher, J.G.M.; Ploegh, H.L.; van Kemenade, F.J.; de Goede, R.E.Y.; Miedema, F. Recl. Trav. Chim. Pays-Bas 1993, 112, 82; Look, G.C.; Fotsch, C.H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182; Winchester, B.; Fleet, G.W. Glycobiology 1992, 2, 199.
7. Ganem, B. Acc. Chem. Res. 1996, 29, 340 and ref. cited therein; van den Broek, L.A.G.M.; Vermaas, D.J.; Heskamp, B.M.; van Boeckel, C.A.A.; Tan, M.C.A.A.; Bolscher, J.G.M.; Ploegh, H.L.; van Kemenade, F.J.; de Goede, R.E.Y.; Miedema, F. Recl. Trav. Chim. Pays-Bas 1993, 112, 82; Look, G.C.; Fotsch, C.H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182; Winchester, B.; Fleet, G.W. Glycobiology 1992, 2, 199.
8. Ganem, B. Acc. Chem. Res. 1996, 29, 340 and ref. cited therein; van den Broek, L.A.G.M.; Vermaas, D.J.; Heskamp, B.M.; van Boeckel, C.A.A.; Tan, M.C.A.A.; Bolscher, J.G.M.; Ploegh, H.L.; van Kemenade, F.J.; de Goede, R.E.Y.; Miedema, F. Recl. Trav. Chim. Pays-Bas 1993, 112, 82; Look, G.C.; Fotsch, C.H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182; Winchester, B.; Fleet, G.W. Glycobiology 1992, 2, 199.
9. Ganem, B. Acc. Chem. Res. 1996, 29, 340 and ref. cited therein; van den Broek, L.A.G.M.; Vermaas, D.J.; Heskamp, B.M.; van Boeckel, C.A.A.; Tan, M.C.A.A.; Bolscher, J.G.M.; Ploegh, H.L.; van Kemenade, F.J.; de Goede, R.E.Y.; Miedema, F. Recl. Trav. Chim. Pays-Bas 1993, 112, 82; Look, G.C.; Fotsch, C.H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182; Winchester, B.; Fleet, G.W. Glycobiology 1992, 2, 199.
10. Brandi, A.; Cicchi, S.; Cordero, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806 and ref. 10-14 cited therein; Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron : Asymmetry 1996, 7, 1659.
11. Brandi, A.; Cicchi, S.; Cordero, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806 and ref. 10-14 cited therein; Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron : Asymmetry 1996, 7, 1659.
12. Bischoff, J.; Kornfeld, R. Biochem. Biophys. Res. Commun. 1984, 125, 324; Fuhrmann, U.; Bause, E.; Legler, G.; Ploegh, H. Nature 1984, 307, 755.
13. Bischoff, J.; Kornfeld, R. Biochem. Biophys. Res. Commun. 1984, 125, 324; Fuhrmann, U.; Bause, E.; Legler, G.; Ploegh, H. Nature 1984, 307, 755.
14. de Gasperi, R.; Daniel, P.F.; Warren, C.D. J. Biol. Chem. 1992, 267, 9706.
15. White, S.L.; Nagai, T.; Akijama, S.K.; Reeves, E.J.; Grzegorsewski, K.; Olden, K. Cancer Commun. 1991, 3, 83; Olden, K.; Breton, P.; Grzegorsewski K.; Yasuda, Y.; Gause, B.L.; Oredipe, O.A.; Newton, S.A.; White, S.L. Pharmacol. Ther. 1991, 50, 285.
16. White, S.L.; Nagai, T.; Akijama, S.K.; Reeves, E.J.; Grzegorsewski, K.; Olden, K. Cancer Commun. 1991, 3, 83; Olden, K.; Breton, P.; Grzegorsewski K.; Yasuda, Y.; Gause, B.L.; Oredipe, O.A.; Newton, S.A.; White, S.L. Pharmacol. Ther. 1991, 50, 285.
17. Fleet, G.W.J.; Nicholas, S.J.; Smith, P.W.; Evans, S.V.; Fellows, L.E.; Nash, R.J. Tetrahedron Lett. 1985, 26, 3127; Wong, C.-H.; Provencher, L.; Porco, J.A.Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D.H. J. Org. Chem. 1995, 60, 1492.
18. Fleet, G.W.J.; Nicholas, S.J.; Smith, P.W.; Evans, S.V.; Fellows, L.E.; Nash, R.J. Tetrahedron Lett. 1985, 26, 3127; Wong, C.-H.; Provencher, L.; Porco, J.A.Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D.H. J. Org. Chem. 1995, 60, 1492.
19. a) Fleet, G.W.J.; Winchester, B.G. US Patent, No. 5,250,703, Oct. 5, 1993, C.A. 120 : 218422g;
20. b) Lundt, I.; Madsen, R.; Al Daher, S.; Winchester, B. Tetrahedron 1994, 50, 7513.
21. 12
22. Johnson, C.R.; Miller, M.W.; Golebiowski, A.; Sundram, H.; Ksebati, M.B. Tetrahedron Lett. 1994, 35, 8991.
23. Martin, O.R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991.
24. Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483; Frérot, E.; Marquis, C.; Vogel, P. Ibid. 1996, 37, 2023.
25. Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483; Frérot, E.; Marquis, C.; Vogel, P. Ibid. 1996, 37, 2023.
26. Vieira, E.; Vogel, P. Helv. Chim. Acta 1982, 65, 1700; Schmidt, R.R.; Beitzke, C.; Forrest, A.K. J. Chem. Soc., Chem. Commun. 1982, 909.
27. Vieira, E.; Vogel, P. Helv. Chim. Acta 1982, 65, 1700; Schmidt, R.R.; Beitzke, C.; Forrest, A.K. J. Chem. Soc., Chem. Commun. 1982, 909.
28. See e.g.: Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395; Emery, F.; Vogel, P. J. Org. Chem. 1995, 60, 5843; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. Ibid. 1995, 60, 8351; Ferritto, R.; Vogel, P. Synlett 1996, 281.
29. See e.g.: Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395; Emery, F.; Vogel, P. J. Org. Chem. 1995, 60, 5843; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. Ibid. 1995, 60, 8351; Ferritto, R.; Vogel, P. Synlett 1996, 281.
30. See e.g.: Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395; Emery, F.; Vogel, P. J. Org. Chem. 1995, 60, 5843; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. Ibid. 1995, 60, 8351; Ferritto, R.; Vogel, P. Synlett 1996, 281.
31. See e.g.: Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395; Emery, F.; Vogel, P. J. Org. Chem. 1995, 60, 5843; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. Ibid. 1995, 60, 8351; Ferritto, R.; Vogel, P. Synlett 1996, 281.
32. See e.g.: Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Vogel, P. Bull. Soc. Chim. Belg. 1990, 99, 395; Emery, F.; Vogel, P. J. Org. Chem. 1995, 60, 5843; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. Ibid. 1995, 60, 8351; Ferritto, R.; Vogel, P. Synlett 1996, 281.
33. a) Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865;
34. b) Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; see also: Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Ronan, B.; Kagan, H.B. Tetrahedron : Asymmetry 1991, 2, 75; Corey, E.J.; Loh, J.-T. Tetrahedron Lett. 1993, 34, 3979.
35. b) Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; see also: Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Ronan, B.; Kagan, H.B. Tetrahedron : Asymmetry 1991, 2, 75; Corey, E.J.; Loh, J.-T. Tetrahedron Lett. 1993, 34, 3979.
36. b) Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; see also: Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Ronan, B.; Kagan, H.B. Tetrahedron : Asymmetry 1991, 2, 75; Corey, E.J.; Loh, J.-T. Tetrahedron Lett. 1993, 34, 3979.
37. b) Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; see also: Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Ronan, B.; Kagan, H.B. Tetrahedron : Asymmetry 1991, 2, 75; Corey, E.J.; Loh, J.-T. Tetrahedron Lett. 1993, 34, 3979.
38. Kraehenbuehl, K.; Vogel, P. Tetrahedron Lett. 1995, 36, 8595.
39. Gemal, A.L.; Luche, L.J. J. Amer. Chem. Soc. 1981, 103, 5454.
40. 3J=5.5, 3.0), 0.93, 0.15, 0.14 (3s).
41. Gartiser, T.; Selve, C.; Delpuech, J.-J. Tetrahedron Lett. 1983, 24, 1609.
42. C : 111.4 (s), 101.4 (d), 97.6, 97.3 (2t), 84.0, 82.6, 82.4, 80.7, 79.0, 72.1 (6d), 68.9 (t), 65.9 (d), 55.9, 55.5 (2q), 53.0 (t), 52.9 (d), 26.1, 24.0 (2q).
43. C: 111.6 (s), 100.0 (d), 97.0, 96.6 (2t), 82.0, 81.6, 81.5, 81.2, 78.0, 70.4, 68.7 (7d), 67.7 (t), 55.8, 55.3 (2q), 52.5 (t), 50.8 (d), 26.6, 24.3 (2q).
44. Under standard conditions and optimal pH, see ref. 3.