A short stereoselective synthesis of the protected uracil 3′-epi-polyoxin C

Tetrahedron Asymmetry

Volumn 22, Issue 2, 2011, Pages 207-214

  Gonda, Jozef ^a   Martinková, Miroslava ^a   Baur, Andrea ^a  

^a P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

5 ISOTHIOCYANATO ALPHA DEXTRO GLUCO HEPT 6 ENFURANOSE; 7 THIOCYANATO ALPHA DEXTRO XYLO HEPT 5 ENFURANOSE; NITROGEN; THYMINE POLYOXIN C; UNCLASSIFIED DRUG; URACIL 3' EPIPOLYOXIN C;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 79952489906     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.02.004     Document Type: Article

References (57)

1. K. Isono, K. Asahi, and S. Suzuki J. Am. Chem. Soc. 91 1969 7490 7505
2. K. Isono, and S. Suzuki Heterocycles 13 1979 333 351
3. K. Isono, J. Nagatsu, Y. Kawashima, and S. Suzuki Agric. Biol. Chem. 29 1965 848 854
4. D. Zhang, and M.J. Miller Curr. Pharm. Des. 5 1999 73 99
5. G.W. Gooday P.J. Kuhn, A.P. Trinci, M.J. Jung, M.W. Goosey, L.G. Copping, Biochemistry of Cell Walls and Membranes in Fungi 1990 Springer Berlin 61
6. R.A.A. Muzzerelli, Chitin 1977 Pergamon Press Oxford 5 44
7. K. Isono J. Antibiot. 41 1988 1711 1739
8. M. Misato, and K. Kakiki M. Siegel, H.D. Sisler, Antifungal Compounds 1977 Dekker New York 277
9. T. Naka, T. Hashizume, and T. Nishimuta Tetrahedron Lett. 12 1971 95 98
10. N.P. Damodaran, G.H. Jones, and J.G. Moffatt J. Am. Chem. Soc. 93 1971 3812 3813
11. H. Ohrui, H. Kuzuhara, and S. Emoto Tetrahedron Lett. 12 1971 4267 4270
12. H. Akita, K. Uchida, and C.-Y. Chen Heterocycles 46 1997 87 90
13. A. Dondoni, F. Junquera, F.L. Merchan, P. Merino, and T. Tejero Tetrahedron Lett. 35 1994 9439 9442
14. A.G.M. Barrett, and S.A. Lebold J. Org. Chem. 55 1990 3853 3857
15. P. Garner, and J.M. Park J. Org. Chem. 55 1990 3772 3776
16. T. Mukaiyama, K. Suzuki, T. Yamada, and F. Tabusa Tetrahedron 46 1990 265 276
17. Y. Auberson, and P. Vogel Tetrahedron Lett. 46 1990 7019 7032
18. H. Akita, K. Uchida, C.-Y. Chen, and K. Kato Chem. Pharm. Bull. 46 1998 1034 1038
19. D.M. Gethin, and N.S. Simpkins Tetrahedron 53 1997 14417 14436
20. A. Chen, E.J. Thomas, and P.D. Wilson J. Chem. Soc., Perkin Trans. 1 1999 3305 3310
21. H. Akita, K. Uchida, and K. Kato Heterocycles 47 1998 157 159
22. H. Kuzuhara, H. Ohrui, and S. Emoto Tetrahedron Lett. 1973 5055 5058
23. F. Tabusa, T. Yamada, K. Suzuki, and K. Mukaiyama Chem. Lett. 1984 405 408
24. N. Chida, K. Koizumi, Y. Kitada, C. Yokoyama, and S. Ogawa J. Chem. Soc., Chem. Commun. 1994 111 113
25. A. Dondoni, F. Junquera, F.L. Merchan, P. Merino, and T. Tejero J. Chem. Soc., Chem. Commun. 1995 2127
26. A. Dondoni, S. Franco, F. Junquera, F.L. Merchan, P. Merino, and T. Tejero J. Org. Chem. 62 1997 5497 5507
27. H. Kuzuhara, and S. Emoto Tetrahedron Lett. 14 1973 5051 5054
28. H. Kuzuhara, M. Kimura, and S. Emoto Carbohydr. Res. 45 1975 245 255
29. J.C. Boehm, and W. Kingsbury J. Org. Chem. 51 1986 2307 2314
30. A.K. Saksena, R.G. Lovey, V.M. Girijavallabhan, A.K. Ganguly, and A.T. McPhail J. Org. Chem. 51 1986 5024 5028
31. P. Garner, and J.M. Park J. Org. Chem. 53 1988 2979 2984
32. D.M. Gethin, and N. Simpkins Tetrahedron 53 1997 14417 14436
33. A.K. Ghosh, and Y. Wang J. Org. Chem. 63 1998 6735 6738
34. E. Krainer, J.M. Becker, and F. Naider J. Med. Chem. 34 1991 174 180
35. J.C. Bohem, and W.D. Kingsbury J. Org. Chem. 51 1986 2307 2314
36. A. Rosenthal, and B.L. Cliff Carbohydr. Res. 79 1980 63 67
37. J. Fiandor, M.-T. Garciá-López, F.G. DelasHeras, and P.P. Méndez-Castrillón Synthesis 1987 978 981
38. S.E. Ward, A.B. Holmes, and R. McCague Chem. Commun. 1997 2085 2086
39. D. Zhang, and M.J. Miller J. Org. Chem. 63 1998 755 759
40. V.K. Aggarwal, and N. Monteiro J. Chem. Soc., Perkin Trans. 1 1997 2531 2537
41. P. Merino, S. Franco, F.L. Merchán, and T. Tejero J. Org. Chem. 65 2000 5575 5589
42. Y.-C. Luo, H.-H. Zhang, Y.-Z. Liu, R.-L. Cheng, and P.-F. Xu Tetrahedron: Asymmetry 20 2009 1174 1180
43. J. Gonda, and M. Bednáriková Tetrahedron Lett. 38 1997 5569 5572
44. J. Gonda, M. Martinková, J. Raschmanová, and E. Balentová Tetrahedron: Asymmetry 17 2006 1875 1882
45. M. Martinková, J. Gonda, and J. Raschmanová Molecules 11 2006 564 573
46. M. Martinková, J. Gonda, J. Raschmanová, and M. Vojtíčková Tetrahedron 63 2007 10603 10607
47. A. Chen, I. Savage, E.J. Thomas, and P.D. Wilson Tetrahedron Lett. 34 1993 6769 6772
48. I. Savage, and E.J. Thomas J. Chem. Soc., Chem. Commun. 1989 717 719
49. J. Gonda, M. Martinková, A. Zadrošová, M. Šoteková, J. Raschmanová, P. Čonka, E. Gajdošíková, and C.O. Kappe Tetrahedron Lett. 48 2007 6912 6915
50. E. Gajdošíková, M. Martinková, J. Gonda, and P. Čonka Molecules 13 2008 2837 2847
51. J. Ammenn, K.-H. Altmann, and D. Belluš Helv. Chim. Acta 80 1997 1589 1606
52. H. Vorbrüggen, K. Krolikiewicz, and B. Benua Chem. Ber. 114 1981 1234 1255
53. H. Vorbrüggen, and U. Niedballa J. Org. Chem. 39 1974 3654 3674
54. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112 122
55. A.L. Spek J. Appl. Crystallogr. 36 2003 7 13
56. L. Kniežo, J. Bernát, and M. Martinková Chem. Papers 48 1994 103 107
57. jaguar 7.7, Schrodinger, LLC, New York, NY, 2010.