N-Glycosylhydroxylamines as masked polyhydroxylated chiral nitrones in cycloaddition reactions: An access to pyrrolizidines

Heterocycles

Volumn 79, Issue C, 2009, Pages 883-896

  Marradi, Marco ^a   Corsi, Massimo ^a   Cicchi, Stefano ^a   Bonanni, Marco ^a   Cardona, Francesca ^a   Goti, Andrea ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Alkaloid; Carbohydrate; Glycosidase Inhibitor; Nitrogen Heterocycle; Solvent Free Condition

Indexed keywords

EID: 67651087395     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(D)59     Document Type: Article

References (75)

1. Tufariello J.J. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry (1984), John Wiley & Sons, New York
2. Confalone P.N., and Huie E.M. Org. React. 36 (1988) 1
3. Torssell K.B.G. In: Feuer H. (Ed). Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis (1988), VCH Publishers, New York
4. Jones R.C.F., and Martin J.N. In: Padwa A., and Pearson W.H. (Eds). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (2002), John Wiley & Sons, New York
5. Bloch R. Chem. Rev. 98 (1998) 1407
6. Enders D., and Reinhold U. Tetrahedron: Asymmetry 8 (1997) 1895
7. Lombardo M., and Trombini C. Synthesis (2000) 759
8. Merino P. In: Padwa A. (Ed). Science of Synthesis Vol. 27 (2004), Thieme, Stuttgart
9. Cardona F., and Goti A. Angew. Chem. Int. Ed. 44 (2005) 7832
10. Masson G., Py S., and Vallée Y. Angew. Chem. Int. Ed. 41 (2002) 1772
11. Masson G., Cividino P., Py S., and Vallée Y. Angew. Chem. Int. Ed. 42 (2003) 2265
12. Riber D., and Skrydstrup T. Org. Lett. 5 (2003) 229
13. Burchak O.N., Philouze C., Chavant P.Y., and Py S. Org. Lett. 10 (2008) 3021
14. Frederickson M. Tetrahedron 53 (1997) 403
15. Gothelf K.V., and Jørgensen K.A. Chem. Rev. 98 (1998) 863
16. Koumbis A.E., and Gallos J.K. Curr. Org. Chem. 7 (2003) 585
17. Osborn H.M.I., Gemmell N., and Harwood L.M. J. Chem. Soc., Perkin Trans. 1 (2002) 2419
18. Revuelta J., Cicchi S., Goti A., and Brandi A. Synthesis (2007) 485
19. Merino P., Franco S., Merchan F.L., and Tejero T. Synlett (2000) 442
20. Lombardo M., and Trombini C. Curr. Org. Chem. 6 (2002) 695
21. Kleban M., Hilgers P., Greul J.N., Kugler R.D., Li J., Picasso S., Vogel P., and Jäger V. Chem Bio Chem 2 (2001) 365
22. Palmer A.M., and Jäger V. Eur. J. Org. Chem. (2001) 1293
23. Bonanni M., Marradi M., Cardona F., Cicchi S., and Goti A. Beilstein J. Org. Chem. 3 (2007) 44 doi: 10.1186/1860-5397-3-44
24. Vasella A. Helv. Chim. Acta 60 (1977) 426
25. Merino P., Franco S., Merchan F.L., and Tejero T. Synth. Commun. 27 (1997) 3529
26. Cicchi S., Corsi M., Marradi M., and Goti A. Tetrahedron Lett. 43 (2002) 2741
27. Cicchi S., Marradi M., Corsi M., Faggi C., and Goti A. Eur. J. Org. Chem. (2003) 4152
28. Dondoni A., and Perrone D. Tetrahedron Lett. 40 (1999) 9375
29. Dondoni A., Giovannini P.P., and Perrone D. J. Org. Chem. 67 (2002) 7203
30. Vasella A. Helv. Chim. Acta 60 (1977) 1273
31. Vasella A., and Voeffray R. J. Chem. Soc., Chem. Commun. (1981) 97
32. Vasella A., and Voeffray R. Helv. Chim. Acta 65 (1982) 1134
33. Vasella A., and Voeffray R. Helv. Chim. Acta 65 (1982) 1953
34. Vasella A., Voeffray R., Pless J., and Huguenin R. Helv. Chim. Acta 66 (1983) 1241
35. Kasahara K., Iida H., and Kibayashi C. J. Am. Chem. Soc. 108 (1986) 4647
36. Mzengeza S., and Whitney R.A. J. Org. Chem. 53 (1988) 4074
37. Kasahara K., Iida H., and Kibayashi C. J. Org. Chem. 54 (1989) 2225
38. Machetti F., Cordero F.M., De Sarlo F., Guarna A., and Brandi A. Tetrahedron Lett. 37 (1996) 4205
39. Tamura O., Mita N., Kusaka N., Suzuki H., and Sakamoto M. Tetrahedron Lett. 38 (1997) 429
40. Chiacchio U., Corsaro A., Gumina G., Rescifina A., Iannazzo D., Piperno A., Romeo G., and Romeo R. J. Org. Chem. 64 (1999) 9321
41. Chiacchio U., Rescifina A., Corsaro A., Pistarà V., Romeo G., and Romeo R. Tetrahedron: Asymmetry 11 (2000) 2045
42. Tamura O., Kanoh A., Yamashita M., and Ishibashi H. Tetrahedron 60 (2004) 9997
43. Tamura O., Iyama N., and Ishibashi H. J. Org. Chem. 69 (2004) 1475
44. Huber R., Knierzinger A., Obrecht J.-P., and Vasella A. Helv. Chim. Acta 68 (1985) 1730
45. Bernet B., Krawczyk E., and Vasella A. Helv. Chim. Acta 68 (1985) 2299
46. Huber R., and Vasella A. Helv. Chim. Acta 70 (1987) 1461
47. Huber R., and Vasella A. Tetrahedron 46 (1990) 33
48. Lantos I., Flisak J., Liu L., Matsuoka R., Mendelson W., Stevenson D., Tubman K., Tucker L., Zhang W.-Y., Adams J., Sorenson M., Garigipati R., Erhardt K., and Ross S. J. Org. Chem. 62 (1997) 5385
49. Mita N., Tamura O., Ishibashi H., and Sakamoto M. Org. Lett. 4 (2002) 1111
50. Mancini F., Piazza M.G., and Trombini C. J. Org. Chem. 56 (1991) 4246
51. Rohloff J.C., Alfredson T.V., and Schwartz M.A. Tetrahedron Lett. 35 (1994) 1011
52. Basha A., Henry R., McLaughlin M.A., Ratajczyk J.D., and Wittenberger S.J. J. Org. Chem. 59 (1994) 6103
53. Fässler R., Frantz D.E., Oetiker J., and Carreira E.M. Angew. Chem. Int. Ed. 41 (2002) 3054
54. Patel S.K., Py S., Pandya S.U., Chavant P.Y., and Vallée Y. Tetrahedron: Asymmetry 14 (2003) 525
55. Dondoni A., and Perrone D. Tetrahedron 59 (2003) 4261
56. Dondoni A., and Nuzzi A. J. Org. Chem. 71 (2006) 7574
57. Bonanni M., Marradi M., Cicchi S., Faggi C., and Goti A. Org. Lett. 7 (2005) 319
58. Bonanni M., Marradi M., Cicchi S., and Goti A. Synlett (2008) 197
59. For examples of intramolecular cycloadditions of such compounds, see. Jachak S.M., Karche N.P., and Dhavale D.D. Tetrahedron Lett. 42 (2001) 4925
60. Ferner R.J., and Prasit P. J. Chem. Soc., Chem. Commun. (1981) 983
61. Argyropoulos N.G., Gkizis P., and Coutouli-Argyropoulou E. Tetrahedron 64 (2008) 8752
62. Cicchi S., Marradi M., Vogel P., and Goti A. J. Org. Chem. 71 (2006) 1614
63. 3 at rt showed a 94:6 7/8 equilibrium mixture (see ref. 7).
64. DeShong P., Dicken C.M., Leginus J.M., and Whittle R.R. J. Am. Chem. Soc. 106 (1984) 5598
65. Fray M.J., Jones R.H., and Thomas E.J. J. Chem. Soc., Perkin Trans. 1 (1985) 2753
66. Similar values have been reported for related cycloadducts (see ref. 17).
67. An analogous isomerization induced by a monosubstituted hydroxylamine has been observed. Aurich H.G., Franzen H., and Rohr H.G. Tetrahedron 50 (1994) 7417
68. For similar oxidative ring-opening processes of isoxazolidines to aminoketones induced by strong bases, see. Cordero F.M., Machetti F., De Sarlo F., and Brandi A. Gazz. Chim. Ital. 127 (1997) 25
69. Murahashi S.-I., Kodera Y., and Hosomi T. Tetrahedron Lett. 29 (1988) 5949
70. Hootelé C., Ibebeke-Bomangwa W., Driessens F., and Sabil S. Bull. Soc. Chim. Belg. 96 (1987) 57
71. Tufariello J.J., and Ali Sk.A. J. Am. Chem. Soc. 101 (1979) 7114
72. Goti A., Cicchi S., Cacciarini M., Cardona F., Fedi V., and Brandi A. Eur. J. Org. Chem. (2000) 3633
73. Zhong W., Kuntz D.A., Ember B., Singh H., Moremen K.W., Rose D.R., and Boons J.-G. J. Am. Chem. Soc. 130 (2008) 8975
74. Shah N., Kuntz D.A., and Rose D.R. Proc. Natl. Acad. Sci. U.S.A. 105 (2008) 9570
75. The structure of a dGMII·15 complex has been resolved (D. A. Kuntz and D. R. Rose, personal communication). Full details will be given in a forthcoming full paper.