Highly regioselective oxirane ring-opening of a versatile epoxypyrrolidine precursor of new imino-sugar-based sphingolipid mimics

European Journal of Organic Chemistry

Volumn , Issue 15, 2009, Pages 2474-2489

  Rives, Arnaud ^a   Génisson, Yves ^a   Faugeroux, Vanessa ^a   Zedde, Chantal ^a   Lepetit, Christine ^b   Chauvin, Remi ^b   Saffon, Nathalie ^c   Andrieu Abadie, Nathalie ^d   Colié, Sandra ^d   Levade, Thierry ^d   Baltas, Michel ^a  

^a Université Paul Sabatier Toulouse III   (France)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^c UNIVERSITÉ PAUL SABATIER   (France)

^d INSERM   (France)

Author keywords

Asymmetric synthesis; Density functional calculations; Inhibitors; Regioselectivity; Sphingolipids

Indexed keywords

EID: 66149133312     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900100     Document Type: Article

References (37)

1. N. Asano, R. J. Nash, R. J. Molyneux, G. W. J. Fleet, Tetrahedron: Asymmetry 2000, 11, 1645-1680.
2. N. Asano, Curr. Top. Med. Chem. 2003, 3, 471-484.
3. a) For a review of imino sugars as potential antiviral agents, see: T. M. Wrodnigg, A. J. Steiner, B. J. Ueberbachere, Curr Top Med Chem 2003, 3, 513-523;
4. b) for a review of imino sugars in anti-cancer therapy, see: P. Greimel, J. Spreitz, A. E. Stutz, T. M. Wrodnigg, Anti-Cancer Agents Med. Chem. 2008, 8,77-85.
5. a) For Miglitol and type-2 Diabetes mellitus, see: L. J. Scott, C. M. Spencer, Drugs 2000, 59, 521-549;
6. b) for Miglustat and Gaucher's disease see: R. H. Lachman, Curr. Opin. Invest. Drugs 2003, 4, 472-479.
7. C. Norez, S. Noel, M. Wilke, M. Bijvelds, H. Jorna, P. Melin, H. DeJonge, F. Becq, FEBS Lett. 2006, 580, 2081-2086.
8. T. Ayad, Y. Genisson, M. Baltas, Curr. Org. Chem. 2004, 8, 1211-1233.
9. For representative leading references, see: a) X. Zhu, K. A. Sheth, S. Li, H.-H. Chang, J.-Q. Fan, Angew. Chem. Int. Ed. 2005, 44, 7450-7453;
10. b) P. Compain, O. R. Martin, C. Boucheron, G. Godin, L. Yu, K. Ikeda, N. Asano, ChemBioChem 2006, 7, 1356-1359;
11. c) T. Wennekes, R. J. B. H.N. van den Berg, W. Donker, G. A. van der Marel, A. Strijland, J. M. F. G. Aerts, H. S. Overkleeft, J. Org. Chem. 2007, 72, 1088 -1097.
12. a) T. Ayad, Y. Genisson, M. Baltas, L. Gorrichon, Synlett 2001, 6, 866-868;
13. b) T. Ayad, Y. Genisson, M. Baltas, L. Gorrichon, Chem. Commun. 2003, 582-583;
14. c) T. Ayad, Y. Genisson, S. Broussy, M. Baltas, L. Gorrichon, Eur. J. Org. Chem. 2003, 2903-2910;
15. d) T. Ayad, Y. Genisson, M. Baltas, Org. Biomol. Chem. 2005, 3, 2626-2631.
16. Part of this work has been published as a preliminary communication: V. Faugeroux, Y. Genisson, N. Andrieu-Abadie, S. Colie, T. Levade, M. Baltas, Org. Biomol. Chem. 2006, 4, 4437-4439.
17. C. H. Behrens, K. B. Sharpless, J. Org. Chem. 1985, 50, 5696-5704.
18. M. Alcon, A. Moyano, M. A. Pericas, A. Riera, Tetrahedron: Asymmetry 1999, 10, 4639-4651.
19. For a related precedent, see: Y. Tsuzuki, K. Chiba, K. Mizuno, K. Tomita, K. Suzuki, Tetrahedron: Asymmetry 2001, 12, 2989-2997.
20. N. Iranpoor, Z. Tarrian, Z. Movahedi, Synthesis 1996, 1473-1476.
21. B. H. Lipshutz, R. S. Wilhelm, J. A. Kozlowski, D. Parker, J. Org. Chem. 1984, 49, 3928-3938.
22. C. Herdeis, A. Aschenbrenner, A. Kirfel, F. Schwabenlander, Tetrahedron: Asymmetry 1997, 8, 2421-2432.
23. M. A. Tius, A. H. Fauq, J. Org. Chem. 1983, 48, 4131-4132.
24. J. Stichler-Bonaparte, A. Vasella, Helv. Chim. Acta 2001, 84, 2355-2376.
25. For the opening of a related bicyclic oxirane with a hydride source, see: C. M. Huwe, S. Blechert, Tetrahedron Lett. 1995, 36, 1621-1624. For the opening of a pyroglutamic acid derived epoxypyrrolidine with several other nucleopliles, see ref.[15]
26. a) J. R. Pliego Jr., J. M. Riveros, J. Phys. Chem. A 2001, 105, 7241 -7247;
27. b) C. P. Kelly, C. J. Cramer, D. G. Truhlar, J. Chem. Theory Comput. 2005, 1, 1133-1152.
28. G. S. Hammond, J. Am. Chem. Soc. 1955, 77, 334-338.
29. T. D. Butters, Expert Opin. Pharmacother. 2007, 8, 427-435.
30. Z. Q. Yu, A. R. Sawkar, J. W. Kelly, FEBS J. 2007, 274, 4944-4950.
31. B. Segui, N. Andrieu-Abadie, J. P. Jaffrezou, H. Benoist, T. Levade, Biochim. Biophys. Acta Biomembr. 2006, 1758, 2104-2120.
32. S. Lahiri, A. H. Futerman, Cell Mol. Life Sci. 2007, 64, 2270-2284.
33. N. S. Radin, Biochem. Pharmacol. 1999, 57, 589-595.
34. V. Gouaze-Anderson, M. C. Cabot, Biochim Biophys Acta Biomembr. 2006, 1758, 2096-2103.
35. The conformers shown in Figure 8were generated on a Silicon Graphics workstation using the Biosym Tech. Inc. Insight II Dicover program (CVFF force field). The ceramide structure was derived from X-ray data obtained from the Cambridge Crystallographic Database and proceeding from: P.-G. Nyholm, I. Pascher, S. Sundell, Chem. Phys. Lipids 1990, 52, 1-10.
36. M.J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. W. Johnson, W. Wong, C. Gonzalez, J. A. Pople, GAUSSIAN 03, (Revision B.05), Gaussian Inc., Pittsburgh, PA, 2003.
37. S. Noury, X. Krokidis, F. Fuster, B. Silvi, Comput. Chem. 1999, 23, 597-604.