Total syntheses of hyacinthacine A2 and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone

Tetrahedron Letters

Volumn 44, Issue 11, 2003, Pages 2315-2318

  Cardona, Francesca ^a   Faggi, Enrico ^a   Liguori, Francesca ^a   Cacciarini, Martina ^a   Goti, Andrea ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Carbohydrates; Enantiospecific synthesis; Glycosidases inhibitors; Nitrones; Pyrrolizidine alkaloids

Indexed keywords

7 DEOXYCASUARINE; CARBOHYDRATE DERIVATIVE; HYACINTHACINE A2; ISOXAZOLIDINE DERIVATIVE; NITRONE; PYRROLIZIDINE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037430434     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00239-9     Document Type: Article

References (46)

1. Hartmann T., Witte L. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. 9:1996;155-233 Elsevier, Oxford.
2. Nash R.J., Fellows L.E., Dring J.V., Fleet G.W.J., Derome A.E., Hamor T.A., Scofield A.M., Watkin D.J. Tetrahedron Lett. 29:1988;2487-2490.
3. Molyneux R.J., Benson M., Wong R.Y., Tropea J.E., Elbein A.D. J. Nat. Prod. 51:1988;1198-1206.
4. Nash R.J., Watson A.A., Asano N. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. 11:1996;375-376 Elsevier, Oxford.
5. Asano N., Kuroi H., Ikeda K., Kizu H., Kameda Y., Kato A., Adachi I., Watson A.A., Nash R.J., Fleet G.W. J. Tetrahedron: Asymmetry. 11:2000;1-8.
6. Nash R.J., Thomas P.I., Waigh R.D., Fleet G.W.J., Wormald M.R., Lilley P.M., de Q., Watkin D.J. Tetrahedron Lett. 35:1994;7849-7852.
7. Wormald M.R., Nash R.J., Watson A.A., Bhadoria B.K., Langford R., Sims M., Fleet G.W.J. Carbohydr. Lett. 2:1996;169-174.
8. Asano N., Kato A., Miyauchi M., Kizu H., Kameda Y., Watson A.A., Nash R.J., Fleet G.W.J. J. Nat. Prod. 61:1998;625-628.
9. 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. 316:1999;95-103.
10. Yamashita T., Yasuda K., Kizu H., Kameda Y., Watson A.A., Nash R.J., Fleet G.W.J., Asano N. J. Nat. Prod. 65:2002;1875-1881.
11. Tropea J.E., Molyneux R.J., Kaushal G.P., Pan Y.T., Mitchell M., Elbein A.D. Biochemistry. 28:1989;2027-2034.
12. Wormald M.R., Nash R.J., Hrnicar P., White J.D., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 9:1998;2549-2558.
13. Nash R.J., Fellows L.E., Dring J.V., Fleet G.W.J., Girdhar A., Ramsden N.G., Peach J.M., Hegarty M.P., Scofield A.M. Phytochemistry. 29:1990;111-114.
14. Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 11:2000;1645-1680.
15. Watson A.A., Fleet G.W.J., Asano N., Molyneux R.J., Nash R.J. Phytochemistry. 56:2001;265-295. and references cited therein.
16. Alexines and australines: (a) Denmark, S. E.; Herbert, B. J. Am. Chem. Soc. 1998, 120, 7357-7358;
17. (b) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359-7360;
18. (c) Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046-3056;
19. (d) Denmark, S. E.; Herbert, B. J. Org. Chem. 2000, 65, 2887-2896;
20. (e) Pearson, W. H.; Hines, J. V. J. Org. Chem. 2000, 65, 5785-5793;
21. (f) Yoda, H.; Katoh, H.; Takabe, K. Tetrahedron Lett. 2000, 41, 7661-7665;
22. (g) Romero, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 8264-8268;
23. (h) White, J. D.; Hrnciar, P. J. Org. Chem. 2000 65, 9129-9142;
24. (i) Denmark, S. E.; Cottell, J. J. J. Org. Chem. 2001, 66, 4276-4284.
25. Hyacinthacines: (a) Rambaud, L.; Compain, P.; Martin, O. R. Tetrahedron: Asymmetry 2001, 12, 1807-1809;
26. (b) Izquierdo, I.; Plaza, M. T.; Robles, R.; Franco, F. Tetrahedron: Asymmetry 2001, 12, 2481-2487;
27. (c) Izquierdo, I.; Plaza, M. T.; Franco, F. Tetrahedron: Asymmetry 2002, 13, 1581-1585;
28. (d) Yoda, H.; Asai, F.; Takabe, K. Synlett 2000, 1001-1003.
29. Casuarine and analogs: (a) Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311-1314;
30. (b) Denmark, S. E.; Hurd, A. R. J. Org. Chem. 2000, 65, 2875-2886;
31. (c) Bell, A. A.; Pickering, L.; Watson, A. A.; Nash, R. J.; Pan, Y. T.; Elbein, A. D.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 5869-5872;
32. (d) Behr, J.-B.; Erard, A.; Guillerm, G. Eur. J. Org. Chem. 2002, 1256-1262.
33. For our recent work on the synthesis of necine bases, see: (a) Goti, A.; Cicchi, S.; Cacciarini, M.; Cardona, F.; Fedi, V.; Brandi, A. Eur. J. Org. Chem. 2000, 3633-3645;
34. (b) Goti, A.; Cacciarini, M.; Cardona, F.; Cordero, F. M.; Brandi, A. Org. Lett. 2001, 3, 1367-1369;
35. (c) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett 1997, 577-579.
36. All new compounds were fully characterized and gave satisfactory spectroscopic and analytical data.
37. 4: C, 74.80; H, 6.52; N, 3.35. Found: C, 74.51; H, 6.78; N, 3.01%.
38. Fleet J., Smith P. Tetrahedron. 42:1986;5685-5692.
39. Tejima S., Fletcher H.J. J. Org. Chem. 28:1963;2999-3001.
40. For recent related syntheses of nitrones from sugars, see: (a) Holzapfel, C. W.; Crous, R. Heterocycles 1998, 48, 1337-1342;
41. (b) Cicchi, S.; Corsi, M.; Brandi, A.; Goti, A. J. Org. Chem. 2002, 67, 1678-1681;
42. (c) Tamura, O.; Toyao, A.; Ishibashi, H. Synlett 2002, 1344-1346;
43. (d) Duff, F. J.; Vivien, V.; Wightman, R. H. Chem. Commun. 2000, 2127-2128.
44. Liguori, F. Tesi di Laurea, University of Firenze, 1999.
45. An alternative approach from L-xylose, which gave a better yield of 8 but contaminated with a regioisomer, will be reported in a forthcoming full paper.
46. Ishikawa T., Tajima Y., Fukui M., Saito S. Angew. Chem., Int. Ed. Engl. 35:1996;1863-1864.