Azasteroids derived from fusidic acid

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 24, 1998, Pages 4121-4128

  Murphy, William S ^a   Sarsam, Basil ^a   Ferguson, George ^b   Gallagher, John F ^b  

^a UNIVERSITY COLLEGE CORK   (Ireland)

^b UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748736746     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807082b     Document Type: Article

References (61)

1. (a) W. O. Godtfredsen, Fusidic Acid and Some Related Antibiotics, Aarhuus Stiftsbogtrykkerie, Copenhagen, 1967;
2. (b) W. O. Godtfredsen, W. von Daehne, S. Vangedal, D. Arigoni, A. Marquet and A. Melera, Tetrahedron, 1965, 21, 3505;
3. (c) A. Cooper and D. C. Hodgkin, Tetrahedron, 1968, 24, 909.
4. (a) Ref. 1, pp. 47-49;
5. (b) W. O. Godtfredsen, N. Rastrup-Anderson, S. Vangedal and W. D. Ollis, Tetrahedron, 1979, 35, 2419.
6. R. E. Gawley, Org. React. (N. Y.), 1988, 35, 1.
7. See for example: T. G. Back, J. H.-L. Chan and M. Parvez, Synthesis, 1995, 162;
8. T. G. Back and N.-X. Hu, Tetrahedron, 1993, 49, 337;
9. R. E. Dolle, H. S. Allaudeen and L. I. Kruse, J. Med. Chem., 1990, 33, 877;
10. M. Brandt and M. A. Levy, Biochemistry, 1989, 28, 140;
11. G. H. Rasmusson, G. F. Reynolds, N. G. Steinberg, E. Walton, G. F. Patel, T. Liang, M. A. Casciari, A. H. Cheung, J. R. Brooks and C. J. Berman, J. Med. Chem., 1986, 29, 2298.
12. (a) W. O. Godtfredsen and W. von Daehne, Br. Pat. 1129105, 1968;
13. (b) I. Bacso and P. A. Diassi, US Pat. 3347879, 1967;
14. (c) I. Bacso and P. A. Diassi, US Pat. 3391171, 1968;
15. (d) P. A. Diassi and G. W. Krakower, US Pat. 3352854, 1967;
16. (c) P. A. Diassi, US Pat. 3376324, 1968.
17. G. Rasmusson, G. F. Reynolds, T. Utne, R. B. Jobson, R. L. Primka, C. Berman and J. R. Brooks, J. Med. Chem., 1984, 27, 1690;
18. Ch. Catmoutsis and P. Catsoulacos, J. Chem. Eng. Data, 1987, 32, 122;
19. P. Catsoulacos and D. Catsoulacos, J. Heterocycl. Chem., 1993, 30, 1;
20. J. L. Brianso and J. F. Piniella, Afinidad, 1987, 44, 372;
21. Ch. Catmoutsis and P. Catsoulacos, J. Heterocycl. Chem., 1988, 25, 1617;
22. A. Anastasiou, P. Catsoulacos, A. Papageorgiou and E. Margariti, J. Heterocycl. Chem., 1994, 31, 367.
23. H. Sinsh, V. K., Kapoor and D. Paul, Progr. Med. Chem., 1979, 16, 103;
24. R. J. Marshall, I. McIndewar, J. A. M. Peters, N. P. Van Vliet and F. J. Zeelen, Eur. J. Med. Chem., 1984, 19, 43;
25. A. H. Siddiqui, M. Memariani, D. Ramesh, A. H. U. Siddiqui and V. Uma Maheshwar Rao, J. Indian Chem. Soc., 1990, 67, 39;
26. J. J. Deadman, R. McCacue and M. Jarman, J. Chem. Soc., Perkin Trans. 1, 1991, 2413;
27. R. S. Chen, Eur. Pat. Appl. EP, 478,910, 1992;
28. D. Paul Jindal, R. Gupta and J. Abraham, Indian J. Chem., Sect. B, 1994, 33B, 499;
29. M. Han and D. F. Covey, J. Org. Chem., 1996, 61, 7614;
30. R. Gupta, D. Pathak and D. Jindal, Eur. J. Med. Chem., 1996, 31, 241;
31. K. Bhandari, V. L. Sharma and C. M. Singh, Indian J. Chem., Sect. B, 1997, 36B, 352.
32. H. Sucinome, M. Kaji and S. Yamada, J. Chem. Soc., Perkin Trans. 1, 1988, 321.
33. J. A. Zedric and J. Iriarte, J. Org. Chem., 1962, 27, 175.
34. See for example: J. March, Advanced Organic Chemistry, Wiley, New York, 1992, 4th edn., pp. 1054-1055; 1095-1097.
35. W. O. Godtfredsen and S. Vangedal, Tetrahedron, 1962, 18, 1029.
36. G. W. Krakower, H. A. Van Dine, P. A. Diassi and I. Bacso, J. Org. Chem., 1967, 32, 184.
37. K. Tsuda and R. Hayatsu, J. Am. Chem. Soc., 1956, 78, 4107.
38. (a) K. Oka and S. Hara, Chem. Ind. (London), 1968, 911;
39. (b) M. Anastasia, P. Allevi, P. Ciuffred and A. Fiecchi, J. Chem. Soc., Perkin Trans. 1, 1986, 2123.
40. J. W. Akitt, in NMR and Chemistry. An Introduction to the Fourier Transform-Multinuclear Era, 2nd edn., Chapman and Hall, London, 1983, pp. 29-32.
41. F. H. Allen, O. Kennard and R. Taylor, Acc. Chem. Res., 1983 16 146.
42. G. Neef, U. Eder, G. Haffer, R. Wiechert and P. Schonhalzer, Chem. Ber., 1977, 110, 3377.
43. R. Freire, J. A. Salazar, E. Suarez, C. Betancor, D. Melian, T. Prange and C. Pascard, J. Chem. Res., 1977, 152, 1824.
44. W. S. Murphy and S. S. Welankiwar, J. Chem. Soc., Perkin Trans. 1, 1976, 710.
45. L. F. Fieser and S. Rajagoplan, J. Am. Chem. Soc., 1949, 71, 3938.
46. J. A. Zderic and J. Iriarte, J. Org. Chem., 1962, 27, 1756.
47. C. G. McCarty, in The Chemistry of the Carbon-Nitrogen Double Bond, ed. S. Patai, Wiley-Interscience, New York, 1970, p. 392.
48. D. Cocker and W. S. Murphy, J. Chem. Soc, Perkin Trans. 1, 1977, 2565.
49. W. S. Murphy, D. Cocker, G. Ferguson and M. Khan, J. Chem. Soc., Perkin Trans. 1, 1979, 1447.
50. R. E. Ireland, R. Giger and S. Kamata, J. Org. Chem., 1977, 42, 1276.
51. P. A. Diassi, I. Bacso, G. W. Krakower and H. A. Van Dine, Tetrahedron, 1966, 22, 3459.
52. P. H. J. Carlsen, T. Katsuki, V. S. Martin and K. B. Sharpless, J. Org. Chem., 1981, 46, 3936.
53. See for example: M. Tanabe, D. M. Yasuda and R. H. Peters, Tetrahedron Lett., 1977, 1481.
54. K. L. Williamson and W. S. Johnson, J. Am. Chem. Soc., 1961, 83, 4623.
55. J. R. Hanson, in Terpenoids and Steroids, The Royal Chemical Society, London, vol. 12, 1983, p. 300.
56. J. Mann, in Secondary Metabolism, 2nd edn., Clarenden Press, Oxford, 1986, pp. 140-141.
57. G. Sheldrick, SHELXS97, Program for the solution of crystal structures, 1997, University of Göttingen, Germany.
58. G. Sheldrick, SHELXS97, Program for the refinement of crystal structures, 1997, University of Göttingen, Germany.
59. C. K. Johnson, ORTEP-A Fortran Thermal Ellipsoid Plot Program, Technical Report ORNL-5138, 1976, Oak Ridge National Laboratory, USA.
60. A. L. Spek, PLUTON Molecular Geometry and Graphics, September 1997 version, University of Utrecht, Utrecht, The Netherlands.
61. E. J. Gabe, Y. LePage, J. P. Charland, F. L. Lee and P. S. White, J. Appl. Crystallogr., 1989, 22, 384.