Synthesis of polyhydroxylated 7-aminopyrrolizidines and 8-aminoindolizidines

Tetrahedron

Volumn 65, Issue 34, 2009, Pages 7056-7063

  Stecko, Sebastian ^a   Jurczak, Margarita ^a   Staszewska Krajewska, Olga ^a   Solecka, Jolanta ^b   Chmielewski, Marek ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b NATIONAL INSTITUTE OF HYGIENE   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,6 TRIHYDROXY 5 (HYDROXYMETHYL) 7 (METHOXYCARBONYLAMINO)PYRROLIZIDINE; 1,2,6 TRIHYDROXY 7 (METHOXYCARBONYLAMINO)PYRROLIZIDINE; 1,2,6,7 TETRAHYDROXY 8 (METHOXYCARBONYLAMINO)INDOLIZIDINE; 7 AMINOPYRROLIZIDINE; 8 AMINOINDOLIZIDINE; ABSOULINE; FURANONE DERIVATIVE; GLYCOSIDASE INHIBITOR; INDOLE DERIVATIVE; ISOABSOULINE; LABURNAMINE; LACTONE; LOLINE; NITRONE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; SLAFRAMINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; DEACETYLATION; ENZYME INHIBITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 67650526384     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.043     Document Type: Article

References (54)

1. Pearson M.S., Mathe-Allainmat M., Fargeas J., and Lebreton J. Eur. J. Org. Chem. 11 (2005) 2159-2167
2. Watson A.A., Fleet G.W.J., Asano N., Molyneux R.J., and Nash R.J. Phytochemistry 56 (2001) 265-295
3. Asanao N., Kato A., and Watson A.A. Mini-Rev. Med. Chem. 1 (2001) 145-154
4. Fleet G.W.J., Fellows L.E., and Winchester B. In: Chadwick P.J., and March J. (Eds). Bioactive Compounds from Plants (1990), Wiley & Sons, Chichester, UK 112-125
5. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645-1680
6. In: Chapleur Y. (Ed). Carbohydrate Mimics (1998), Wiley-VCH, Weinheim
7. Martin O.R., and Compain P. Curr. Top. Med. Chem. 3 (2003) 541-560
8. El Nemr A. Tetrahedron 56 (2000) 8579-8627
9. Felpin F.-X., and Lebreton J. Eur. J. Org. Chem. (2003) 3693-3712
10. Cossy J., and Vogel P. In: Part H., and Atta-ur-Rahman (Eds). Stereoselective Synthesis Vol. 12 (1993), Elsevier, Amsterdam 275-363
11. Herczegh P., Kovacs I., and Sztaricskai F. Chemistry of Biologically Important Hydroxylated Indolizidines: Synthesis of Swainsonine, Castanospermine and Slaframine (1993), Springer, Berlin
12. In: Lukacs G., and Ohno M. (Eds). Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2 (1993), Springer, Berlin 751-828
13. Cipolla L., La Ferla B., and Nicotra F. Curr. Top. Med. Chem. 3 (2003) 485-511
14. Hohenschutz L.D., Bell E.A., Jewess P.J., Lewerothy D.P., Pryce R.J., Arnold E., and Chardy J. Phytochemistry 20 (1981) 811-814
15. Pastuszak I., Molyneux R.J., James L.F., and Elbien A.D. Biochemistry 29 (1990) 1886-1891
16. El Ashry E.S.H., and El Nemr A. Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates (2005), Blackwell, Oxford
17. Vargas-Sanchez M., Couty F., Evano G., Prim D., and Marrot J. Org. Lett. 7 (2005) 5861-5864
18. Tang T., Ruan Y.-P., Ye J.-L., and Huang P.-Q. Synlett (2005) 213-234
19. Giri N., Petrini M., and Profeta R. J. Org. Chem. 69 (2004) 7303-7308
20. Blakemore P.R., Schulze V.K., and White J.W. Chem. Commun. (2000) 1263-1264
21. Schardel C., Grossman R.B., Nagabhzru P., Faulkner J.R., and Mallik U.P. Phytochemistry 68 (2007) 980-996
22. Foresti E., Calmieri G., Petrini M., and Profeta R. Org. Biomol. Chem. 1 (2003) 4275-4281
23. Albano V.G., Gualandi A., Monari M., and Savoia D. J. Org. Chem. 73 (2008) 8376-8381
24. Broggini G., La Rosa C., Pilati T., Terraneo A., and Zecchi G. Tetrahedron 57 (2001) 8322-8332
25. Furneaux R.H., Gainsford G.J., Mason J.M., and Tyler P. Tetrahedron 51 (1995) 12611-12630
26. Pandey G., Dumbre S., Pal S., Khan M., and Shabab M. Tetrahedron 63 (2007) 4756-4761
27. Alcaide B., Almendros P., Alonso J.M., and Aly M.F. Chem.-Eur. J. 9 (2003) 3415-3426
28. Alcaide B., Almendros P., Redondo M.C., and Ruiz M.P. J. Org. Chem. 70 (2005) 8890-8894
29. Hashimoto, S.; Setoi, H.; Takeno, S.; Ito, Y. Patent JP 61,277,685, 1986;
30. Chem. Abstr. 106 (1987) 138253y
31. In: Stütz A. (Ed). Iminosugars as Glycosidases Inhibitors: Norjirmycin and Beyond (1999), Wiley-VCH, Weinheim
32. Compain P., and Martin O.R. Iminosugars: from Synthesis to Therapeutic Applications (2007), John Wiley and Sons, Chichester, UK
33. Socha D., Jurczak M., and Chmielewski M. Carbohydr. Res. 336 (2001) 315-318
34. Rabiczko J., Urbańczyk-Lipkowska Z., and Chmielewski M. Tetrahedron 58 (2002) 1433-1441
35. Socha D., Paśniczek K., Jurczak M., Solecka J., and Chmielewski M. Carbohydr. Res. 341 (2006) 2005-2011
36. Paśniczek K., Socha D., Solecka J., Jurczak M., and Chmielewski M. Can. J. Chem. 84 (2006) 534-539
37. Panfil I., Solecka J., and Chmielewski M. J. Carbohydr. Chem. 25 (2006) 673-684
38. Paśniczek K., Solecka J., and Chmielewski M. J. Carbohydr. Chem. 26 (2007) 195-211
39. Stecko S., Jurczak M., Urbańczyk-Lipkowska Z., Solecka J., and Chmielewski M. Carbohydr. Res. 343 (2008) 2215-2220
40. Stecko S., Solecka J., and Chmielewski M. Carbohydr. Res. 344 (2009) 167-176
41. Stecko S., Paśniczek K., Jurczak M., Solecka J., and Chmielewski M. Pol. J. Chem. 83 (2009) 237-243
42. Stecko S., Paśniczek K., Jurczak M., Urbańczyk-Lipkowska Z., and Chmielewski M. Tetrahedron: Asymmetry 17 (2006) 68-79
43. Stecko S., Paśniczek K., Jurczak M., Urbańczyk-Lipkowska Z., and Chmielewski M. Tetrahedron: Asymmetry 18 (2007) 1085-1093
44. Stecko S., Paśniczek K., Michel C., Milet A., Perez S., and Chmielewski M. Tetrahedron: Asymmetry 19 (2008) 1660-1669
45. Stecko S., Paśniczek K., Michel C., Milet A., Perez S., and Chmielewski M. Tetrahedron: Asymmetry 19 (2008) 2140-2148
46. Song H., Chen W., Wang Y., and Qin Y. Synth. Commun. 35 (2005) 2735-2742
47. Almond M., Simmel J., Thomson A., and Loudon M. Org. Synth. 66 (1988) 132-135
48. Mostowicz D., Beł̇ecki Cz., and Chmielewski M. Synthesis (1991) 273-275
49. Poon K., House S.E., and Dudley G. Synlett (2005) 3142-3144
50. Poon K., and Dudley G. J. Org. Chem. 71 (2006) 3923-3929
51. Poon K., and Dudley G. Org. Synth. 84 (2007) 295-299
52. ALDRICH. ChemFiles 7 (2007) 3
53. Chiacchio U., Casuscelli F., Corsaro A., Librando V., Rescifina A., Romeo R., and Romeo G. Tetrahedron 51 (1995) 5689-5700
54. Armarego W.L.F., and Chai C.L.L. Purification of Laboratory Chemicals. 5th ed. (2003), Butterwoth-Heinemann, Burlington, MA