Synthesis of (6E)-8-Thia- and (14E)-13-Thia-2,3-oxidosqualene: Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

Journal of Organic Chemistry

Volumn 59, Issue 19, 1994, Pages 5803-5809

  Zheng, Yi Feng ^a   Oehlschlager, Allan C ^a   Hartman, Peter G ^b  

^a SIMON FRASER UNIVERSITY   (Canada)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 OXIDO 13 THIASQUALENE; 2,3 OXIDO 8 THIASQUALENE; ENZYME INHIBITOR; LANOSTEROL SYNTHASE; SQUALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA ALBICANS; DRUG SYNTHESIS; ENZYME INHIBITION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0027939023     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00098a048     Document Type: Article

References (43)

1. Schroepfer, G. J., Jr. Ann. Rev. Biochem. 1982, 51, 555.
2. Poulter, C. D.; Rilling, H. J. In Biosynthesis of Isoprenoid Compounds; Porter, J. W., Spurgeon, S. L., Eds.; John Wiley and Sons: New York, 1981; Vol. 1.
3. Oechlschlager, A. C.; Czyzewska, E. In Emerging Targets in Antibacterial and Antifungal Chemotherapy; Sutcliffe, J., Georgopapadakou, N. H., Eds.; Routledge, Chapman & Hall: New York, 1992.
4. Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
5. Boar, R. B.; Couchman, L. A.; Jaques, A. J.; Perkins, M. J. J. Am. Chem. Soc. 1984, 106, 2476.
6. van Tamelen, E. E. J. Am. Chem. Soc. 1982, 104, 6480.
7. van Tamelen, E. E.; James, D. R. J. Am. Chem. Soc. 1977, 99, 950.
8. Johnson, W. S. Angew. Chem., Int. Ed. Engl. 1976,15, 9.
9. Johnson, W. S. Bioorg. Chem. 1976, 5, 51.
10. Johnson, W. S.; Telfer, S. J.; Cheng, S.; Schubert, U. J. Am. Chem. Soc. 1987, 109, 2517.
11. Taton, M.; Benveniste, P.; Rahier, A.; Johnson, W. S.; Liu, H. T.; Sudhakar, A. R. Biochemistry 1992, 31, 7892.
12. Ceruti, M.; Viola, F.; Dosio, F.; Cattel, L.; Bouvier-Nave, P.; Ugliengo, P. J. Chem. Soc., Perkin Trans. 1 1988, 461.
13. Ceruti, M.; Balliano, G.; Viola, F.; Grosa, G.; Rocco, F.; Cattel L. J. Med. Chem. 1992, 35, 3050.
14. Duriatti, A.; Bouvier-Nave, P.; Benveniste, P.; Schuber, F.; Delprino, I.; Balliano, G.; Cattel, L. Biochem. Pharmacol. 1985, 34, 2765.
15. Xiao, X. Y.; Prestwich, G. D. J. Am. Chem. Soc. 1991, 113, 9673.
16. Wannamaker, M. W.; Waid, P. P.; VanSickle, W. A.; McCarthy, J. R.; Wilson, P. K.; Schatzman, G. L.; Moore, W. R. J. Med. Chem. 1992, 35, 3581.
17. Abad, J. L.; Casas, J.; Sanchez-Baeza, F.; Messeguer, A. J. Org. Chem. 1993, 58, 3991.
18. Dodd, D. S.; Oehlschlager, A. C. J. Org. Chem. 1992,57, 2794.
19. Dodd, D. S.; Oehlschlager, A. C.; Georgopapadakou, N. H.; Polak, A. M.; Hartman, P. G. J. Org. Chem. 1992, 57, 7226.
20. Gerst, N.; Duriatti, A.; Schuber, F.; Taton, M.; Benveniste, P.; Rahier, A. Biochem. Pharmacaol. 1988, 37, 1955.
21. Taton, M.; Benveniste, P.; Rahier, A. Pure Appl. Chem. 1987, 59, 287.
22. Mikolatajczyk, M.; Grzejszczak, S.; Chefczynska, A.; Zatorski, A. J. Org. Chem. 1979, 44, 2967.
23. Corey, E. J.; Shulman, J. J. Org. Chem. 1970, 35, 777.
24. Grayson, J. I.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1977, 2263.
25. Gridnev, I. D.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 5351.
26. Murahashi, S. L.; Yamamoto, M.; Yanagisawa, K. I.; Mita, N.; Rondo, K. J. Org. Chem. 1979, 44, 2408.
27. Foa, M.; Santi, R.; Garavaglia, F. J. Organomet. Chem. 1981, 206, C29.
28. Corey, E. J.; d'Alarcao, M.; Kyler, R. S. Tetrahedron Lett. 1985, 26, 3919.
29. Corey, E. J.; Cashman, J. R.; Eckrich, T. M.; Corey, D. R. J. Am. Chem. Soc. 1985, 107, 713.
30. Scholz, D. Liebigs Ann. Chem. 1984, 259.
31. Scholz, D. Synthesis 1983, 944.
32. Katzenellenbogen, J. A.; Lenox, R. S. J. Org. Chem. 1973, 38, 326.
33. Coates, R. M.; Ley, D. A.; Cavender, P. L. J. Org. Chem. 1978, 43, 4915.
34. Mancuso, A. J.; Swem, D. Synthesis 1981, 165.
35. Corey, E. J.; Kim, C. U. Tetrahedron Lett. 1972, 42, 4339.
36. Rand, C. L.; Van Horn, D. E.; Moore, M. W.; Negishi, E. J. Org. Chem. 1981, 46, 4093.
37. Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
38. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. In Spectrometric Identification of organic compounds, 5tb ed.; John Wiley & Sons: New York, 1991; pp 281-283.
39. Corey, E. J.; Jautelat, M.; Oppolzer, W. Tetrahedron Lett. 1967, 2325.
40. Calzada, J. G.; Hooz, J. Org. Synth. 1988, 6, 634.
41. Hooz, J.; Cabezas, J.; Musmanni, S.; Calzada, J. Org. Synth. 1990, 67, 120.
42. Jolidon, S.; Polak-Wyss, A.; Hartman, P. G.; Guerry, P. In Recent Advances in the Chemistry of Anti-infective Agents; Bentley, P. H., Ponsfor, R., Eds.; The Royal Society of Chemistry, 1993; pp 223-233.
43. Jolidon, S.; Polak, A. M.; Guerry, P.; Hartman, P. G. BioChem. Soc. Trans. 1990, 18, 47.