Assembly of the antifungal agent FR-900848 and the CETP inhibitor U-106305: Studies on remarkable multicyclopropane natural products

Chemical Communications

Volumn , Issue 18, 1997, Pages 1693-1700

  Barrett, Anthony G M ^a   Doubleday, Wendel W ^b   Hamprecht, Dieter ^a   Kasdorf, Krista ^a   Tustin, Gary J ^a   White, Andrew J P ^a   Williams, David J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; CARBOXYLIC ACID; CHOLESTEROL ESTER TRANSFER PROTEIN; CYCLOPROPANE DERIVATIVE; FATTY ACID; FR 900848; NATURAL PRODUCT; NUCLEOSIDE; PROTEIN INHIBITOR; U 106305; UNCLASSIFIED DRUG;

BACTERIUM CULTURE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; FERMENTATION; NONHUMAN; REVIEW; SPECTROSCOPY; STEREOCHEMISTRY; STREPTOMYCES; STREPTOVERTICILLUM FERVENS;

EID: 0030867662     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700487g     Document Type: Review

References (54)

1. J. K. Kwon-Chung and J. E. Bennett, Medical Mycology, Lee & Febiger, Philadelphia, 1992.
2. M. Yoshida, M. Ezaki, M. Hashimoto, M. Yamashita, N. Shigematsu, M. Okuhara, M. Kohsaka and K. Horikoshi, J. Antibiot. 1990, 43, 748.
3. H. Tanaka, (Fujisawa Pharmaceutical Co. Ltd.), personal communication.
4. M. Yoshida and K. Horikoshi, US Pat., 4 803 074, 1989.
5. M. Buchert and H. U. Reissig, Chem. Ber., 1992, 125, 2723.
6. D. Niveldt and A. Vos, Acta Crystallogr., Sect. B: Struct. Sci., 1988, 44, 281, 289, 296.
7. A. G. M. Barrett, W. W. Doubleday, G. J. Tustin, A. J. P. White and D. J. Williams, J. Chem. Soc., Chem. Commun., 1994, 1783.
8. A. G. M. Barrett and G. J. Tustin, J. Chem. Soc., Chem. Commun., 1995, 355.
9. A. G. M. Barrett, W. W. Doubleday, K. Kasdorf, G. J. Tustin, A. J. P. White and D. J. Williams, J. Chem. Soc., Chem. Commun., 1995, 407.
10. C. R. Theberge and C. K. Zercher, Tetrahedron Lett., 1994, 35, 9181; 1995, 36, 5495.
11. C. R. Theberge and C. K. Zercher, Tetrahedron Lett., 1994, 35, 9181; 1995, 36, 5495.
12. R. E. J. Cebula, M. R. Hanna, C. R. Theberge, C. A. Verbicky and C. K. Zercher, Tetrahedron Lett., 1995, 36, 5495; C. R. Theberge, C. A. Verbicky and C. K. Zercher, J. Org. Chem., 1996, 61, 8792.
13. R. E. J. Cebula, M. R. Hanna, C. R. Theberge, C. A. Verbicky and C. K. Zercher, Tetrahedron Lett., 1995, 36, 5495; C. R. Theberge, C. A. Verbicky and C. K. Zercher, J. Org. Chem., 1996, 61, 8792.
14. R. W. Armstrong and K. W. Maurer, Tetrahedron Lett., 1995, 36, 357.
15. I. Arai, A. Mori and H. Yamamoto, J. Am. Chem. Soc., 1985, 107, 8524.
16. A. Mori, I. Arai and H. Yamamoto, Tetrahedron, 1986, 42, 6447.
17. Y. Ukaji, M. Nishimura and T. Fujisawa, Chem. Lett., 1992, 61.
18. P. Manganey, F. Grojea, A. Alexakis and J. R. Normant, Tetrahedron Lett., 1988, 29, 2675.
19. P. Manganey, F. Grojea, A. Alexakis and J. R. Normant, Tetrahedron Lett., 1988, 29, 2677.
20. A. B. Charette and H. Juteau, J. Am. Chem. Soc., 1994, 116, 2651.
21. A. B. Charette, S. Prescott and C. Brochu, J. Org. Chem., 1995, 60, 1081; A. B. Charette and J.-F. Marcoux, Synlett, 1995, 1197.
22. A. B. Charette, S. Prescott and C. Brochu, J. Org. Chem., 1995, 60, 1081; A. B. Charette and J.-F. Marcoux, Synlett, 1995, 1197.
23. R. W. Hoffman, Chem. Rev., 1989, 89, 1841 and references cited therein.
24. A. G. M. Barrett, W. W. Doubleday and G. J. Tustin, unpublished observations.
25. T. Tsunoda, M. Suzuki and R. Noyori, Tetrahedron Lett., 1980, 21, 1357.
26. S. G. Davies and G. H. Whitham, J. Chem. Soc., Perkin Trans. 1, 1977, 1346.
27. J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508.
28. A. G. M. Barrett, K. Kasdorf, G. J. Tustin and D. J. Williams, J. Chem. Soc., Chem. Commun., 1995, 1143.
29. A. G. M. Barrett and K. Kasdorf, Chem. Commun., 1996, 325; A. G. M. Barrett and K. Kasdorf, J. Am. Chem. Soc., 1996, 118, in the press.
30. A. G. M. Barrett and K. Kasdorf, Chem. Commun., 1996, 325; A. G. M. Barrett and K. Kasdorf, J. Am. Chem. Soc., 1996, 118, in the press.
31. A. G. M. Barrett, 6th International Kyoto Conference on New Aspects of Organic Chemistry, Kyoto, Japan, November 7-11, 1994.
32. J. R. Falck, B. Mekonnen and J. Yu, 209th American Chemical Society National Meeting, Anaheim, CA, April 2-6, 1995, Abstract 057.
33. M. S. Kuo, R. J. Zielinski, J. I. Cialdella, C. K. Marschke, M. Dupuis, G. P. Li, D. A. Kloosterman, C. H. Spilman and V. P. Marshall, J. Am. Chem. Soc., 1995, 117, 10 629.
34. A. G. M. Barrett, K. Kasdorf and D. J. Williams, J. Chem. Soc., Chem. Commun., 1994, 1781.
35. A. G. M. Barrett, K. Kasdorf, A. J. P. White and D. J. Williams, J. Chem. Soc., Chem. Commun., 1995, 649.
36. A. G. M. Barrett, W. W. Doubleday, K. Kasdorf and G. J. Tustin, J. Org. Chem., 1996, 61, 3280.
37. J. N. Hines, M.J. Peagram, E. J. Thomas and G. H. Whitham, J. Chem. Soc., Perkin Trans. 1, 1973, 2332.
38. M. G. Banwell and R. Onrust, Tetrahedron Lett., 1985, 26, 4543 and references cited therein.
39. R. Hunter, Frank Warren Conference, Orange Free State, South Africa, April 4-7, 1995; R. Clauss, W. Hinz and R. Hunter, Synlett, 1997, 57.
40. R. Hunter, Frank Warren Conference, Orange Free State, South Africa, April 4-7, 1995; R. Clauss, W. Hinz and R. Hunter, Synlett, 1997, 57.
41. A. B. Charette, H. Juteau, H. Lebel and D. Deschênes, Tetrahedron Lett., 1996, 37, 7925.
42. K. A. M. Walker, Tetrahedron. Lett., 1977, 4475.
43. E. D. Laganis and B. L. Chenard, Tetrahedron Lett., 1984, 25, 5831.
44. J. Cabre and A. L. Palomo, Synthesis, 1984, 413.
45. V. Skaric, D. Katalenic, D. Skaric and I. Salaj, J. Chem. Soc., Perkin Trans. 1, 1982, 2091.
46. J. R. Falck, B. Mekonnen, J. Yu and J.-Y. Lai, J. Am. Chem. Soc., 1996, 118, 6096.
47. D. H. R. Barton, D. C. Crich and W. B. Motherwell, Tetrahedron Lett., 1983, 24, 4979.
48. V. Rautenstrauch, Bull. Soc. Chim. Fr., 1994, 131, 515.
49. A. G. M. Barrett, D. Hamprecht, A. J. P. White and D. J. Williams, J. Am. Chem. Soc., 1996, 118, 7863.
50. D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 1991, 113, 7277.
51. A. G. M. Barrett, D. Hamprecht, A. J. P. White and D. J. Williams, unpublished work.
52. A. B. Charette and H. Label, J. Am. Chem. Soc., 1996, 118, 10327.
53. J. B. Baudin, G. Hareau, S. A. Julia, R. Lorne and O. Ruel, Bull. Chim. Soc. Fr., 1993, 130, 856; N. D. Smith, P. J. Kocienski and S. D. A. Street, Synthesis, 1996, 652.
54. J. B. Baudin, G. Hareau, S. A. Julia, R. Lorne and O. Ruel, Bull. Chim. Soc. Fr., 1993, 130, 856; N. D. Smith, P. J. Kocienski and S. D. A. Street, Synthesis, 1996, 652.