Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C 1

Journal of the American Chemical Society

Volumn 128, Issue 46, 2006, Pages 14790-14791

  Lei, Xiaoguang ^a   Porco Jr , John A ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KINAMYCIN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STRUCTURE ANALYSIS;

ANTI-BACTERIAL AGENTS; AZO COMPOUNDS; NAPHTHOQUINONES;

EID: 33845196489     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066621v     Document Type: Article

References (39)

1. Presented in part at the 230th American Chemical Society National Meeting, Washington, DC, August 28-Sept 1, 2005; ORGN abstract 241.
2. For reviews, see (a) Gould, S. J. Chem. Rev. 1997, 97, 2499-2509.
3. (b) Marco-Contelles, J.; Mokina, M. T. Curr. Org. Chem. 2003, 7, 1433-1422.
4. (c) Kumamoto, T.; Ishikawa, T.; Omura, S. Yuki Gosei Kagaku Kyokaishi 2004, 62, 49-58.
5. (a) Ito, S.; Matsuya, T.; Omura, S.; Otani, M.; Nakagawa, A. J. Antibiot. 1970, 23, 315-317.
6. (b) Hata, T.; Omura, S.; Iwai, Y.; Nakagawa, A.; Otani, M. J. Antibiot. 1971, 24, 353-359.
7. (c) Omura, S.; Nakagawa, A.; Yamada, H.; Hata, T.; Furusaki, A. Chem. Pharm. Bull. 1973, 21, 931-940.
8. (a) Seaton, P. J.; Gould, S. J. J. Antibiot. 1989, 42, 189-197.
9. Synthetic studies (b) Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722-5723.
10. (c) Gould, S. J.; Chen, J.; Cone, M. C.; Gore, M. P.; Melville, C. R.; Tamayo, N. J. Org. Chem. 1996, 61, 5720-5721.
11. Lin, H. C.; Chang, S. C.; Wang, N. L.; Chang, L. R. J. Antibiot. 1994, 47, 675-680.
12. Furusaki, A.; Matsui, M.; Watanabe, T.; Omura, S.; Nakagawa, A.; Hata, T. Isr. J. Chem. 1972, 10, 173-187.
13. Gould, S. J.; Tamayo, N.; Melville, C. R.; Cone, M. C. J. Am. Chem. Soc. 1994, 116, 2207-2208.
14. Mithani, S.; Weeratunga, G.; Taylor, N. J.; Dmitrienko, G. I. J. Am. Chem. Soc. 1994, 116, 2209-2210.
15. Mechanistic studies: (a) Laufer, R. S.; Dmitrienko, G. I. J. Am. Chem. Soc. 2002, 124, 1854-1855.
16. (b) Feldman, K. S.; Eastman, K. J. J. Am. Chem. Soc. 2005, 127, 15344-15345.
17. (c) Hasinoff, B. B.; Wu, X.; Yalowich, J. C.; Goodfellow, V.; Laufer, R. S.; Adedayo, O.; Dmitrienko, G. I. Anti-Cancer Drugs 2006, 17, 825-837.
18. Li, C.; Johnson, R. P.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 5095-5106.
19. Hu, Y.; Li, C.; Kulkarni, B. A.; Strobel, G.; Lobkovsky, E.; Torczynski, R. M.; Porco, J. A., Jr. Org. Lett. 2001, 3, 1649-1652.
20. See Supporting Information for complete experimental details.
21. Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. Tetrahedron Lett. 1994, 35, 7171-7172.
22. Busque, F.; Canto, M.; de March, P.; Figueredo, M.; Font, J.; Rodriguez, S. Tetrahedron: Asymmetry 2003, 14, 2021-2032.
23. Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183-7189.
24. Clark, D. A.; Riccardis, F. D.; Nicolaou, K. C. Tetrahedron 1994, 50, 11391-11426.
25. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
26. O'Donnell, C. J.; Burke, S. D. J. Org. Chem. 1998, 63, 8614-8616.
27. Thomas, S.; Huynh, T.; Enriquez-Rios, V.; Singaram, B. Org. Lett. 2001, 3, 3915-3918.
28. Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 1881-1884.
29. Jung, M. E.; Hagenah, J. A. J. Org. Chem. 1987, 52, 1889-1902.
30. Albrecht, B. K.; Williams, R. M. Tetrahedron Lett. 2001, 42, 2755-2757.
31. Bobe, F.; Tunoori, A. R.; Niestroj, A. J.; Gronwald, O.; Maier, M. E. Tetrahedron 1996, 52, 9485-9498.
32. Chong, J. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560-1563.
33. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 7, 639-666.
34. (a) Lindgren, B. O.; Nilsson, T. Acta. Chem. Scand. 1973, 27, 888-890.
35. (b) Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175-1176.
36. de Silva, S. O.; Watanabe, M.; Snieckus, V. J. Org. Chem. 1979, 44, 4802-4808.
37. Lee, A. S.; Hu, Y. J.; Chu, S. F. Tetrahedron 2001, 57, 2121-2126.
38. Andrus, M. B.; Hicken, E. J.; Meredith, E. L.; Simmons, B. L.; Cannon, J. F. Org. Lett. 2003, 5, 3859-3862.
39. Furrow, M. E.; Myers, A. G. J. Am. Chem. Soc. 2004, 126, 12222-12223.