A biogenetically-lnspired synthesis of a ring-D model of kinamycin F: Insights into the conformation of ring D

Organic Letters

Volumn 10, Issue 3, 2008, Pages 381-384

  Chen, Nan ^a   Carrière, Marjolaine B ^a   Laufer, Radoslaw S ^a   Taylor, Nicholas J ^a   Dmitrienko, Gary I ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; KINAMYCIN F; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STREPTOMYCES; SYNTHESIS;

ANTI-BACTERIAL AGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; QUINONES; STREPTOMYCES;

EID: 38949130048     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702650u     Document Type: Article

References (36)

1. Omura, S.; Nakagawa, A.; Yamada, H.; Hata, T.; Furusaki, A. Chem. Pharm. Bull. 1973, 21, 931-940.
2. Gould, S. J.; Tamayo, N.; Melville, C. R.; Cone, M. C. J. Am. Chem. Soc. 1994, 116, 2207-2208.
3. Mithani, S.; Weeratunga, G.; Taylor, N. J.; Dmitrienko, G. I. J. Am. Chem. Soc. 1994, 116, 2209-2210.
4. Proteau, P. J.; Li, Y.; Chen, J.; Williamson, R. T.; Gould, S. J.; Laufer, R. S.; Dmitrienko, G. I. J. Am. Chem. Soc. 2000, 122, 8325-8326.
5. He, H.; Ding, W.-D.; Bernan, V. S.; Richardson, A. D.; Ireland, C. M.; Greenstein, M.; Ellestad, G. A.; Carter, G. T. J. Am. Chem. Soc. 2001, 123, 5362-5363.
6. Gould, S. J. Chem. Rev. 1997, 97, 2499-2509.
7. Kinamycin C (NCS 138425) exhibits potent cytotoxicity against the 60 cancer cell line panel at the National Cancer Institute, and the spectrum of activity is unlike that of any known anticancer agents.
8. Laufer, R. S.; Dmitrienko, G. I. J. Am. Chem. Soc. 2002, 124, 1854-1855 and references cited therein.
9. Feldman, K. S.; Eastman, K. J. J. Am. Chem. Soc. 2006, 128, 12562-12573.
10. Zeng, W.; Ballard, T. E.; Tkachenko, A. G.; Burns, V. A.; Feldheim, D. L.; Melander, C Bioorg. Chem. Lett. 2006, 16, 5148-5151.
11. 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.
12. O'Hara, K. A.; Wu, X.; Patel, D.; Liang, H.; Yalowich, J. C.; Chen, N.; Goodfellow, V.; Adedayo, O.; Dmitrienko, G. I.; Hasinoff, B. B. Free Rad. Biol. Med. 2007, 43, 1132-1144.
13. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722.
14. Birman, V. B.; Zhao, Z.; Guo, L. Org. Lett. 2007, 9, 1223-1225.
15. Liu, W.; Buck, M.; Chen, N.; Shang, M.; Taylor, N. J.; Assoud, A.; Wu, X.; Hasinoff, B. B.; Dmitrienko, G. I. Org. Lett. 2007, 9, 2915-2918.
16. Lei, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2006, 128, 14790-14791.
17. Kumamoto, T.; Kitani, Y.; Tsuchiya, H.; Yamaguchi, K.; Seki, H.; Ishikawa, T. Tetrahedron 2007, 63, 5189-5199.
18. Nicolaou, K. C.; Li, H.; Nold, A. L.; Pappo, D.; Lenzen, A. J. Am. Chem. Soc 2007, 63, 10356-10357.
19. Nicolaou, K. C.; Denton, R. M.; Lenzen, A. A.; Edmonds, D. J.; Li, A.; Milburn, R. R.; Harrison, S. T. Angew. Chem., Int. Ed. 2006, 45, 2076-2081.
20. Gould, S. J.; Chen, J.; Cone, M. C.; Gore, M. P.; Melville, C. R.; Tamayo, N. J. J. Org. Chem. 1996, 61, 5720-5721.
21. Seaton, P. J.; Gould, S. J. J. Antibiot. 1989, 42, 189-197.
22. Young, J.-J.; Ho, S.-N.; Ju, W.-M.; Chang, L.-R. J. Antibiot. 1994, 47, 681-687.
23. Honda, T.; Mizutani, H. Heterocycles 1998, 48, 1753-1757.
24. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560-1563.
25. See the Supporting Information for details.
26. For examples of facile O,O-acyl migrations, see: Akira, K.; Taira, T.; Hasegawa, H.; Sakuma, C.; Shinohara, Y. Drug Metab. Dispos. 1998, 26, 457-464.
27. Thompson, H.; Wolfram, M. L. In Methods in Carbohydrate Chemistry; Whistler, R. L., Wolfram, M. L., BeMiller, J. N., Eds.; Academic Press: New York, 1963; Vol. 2, pp 215-220.
28. Since reagents exist for the dimerization of iodocyclohexanes, 2-iodocyclohexanones and related systems (ref 29), the possibility that related iodohydrins might be converted into dimeric analogues of the kinamycins related to the lomaiviticins is worthy of consideration.
29. (a) Ma, J.; Chan, T.-H. Tetrahedron Lett. 1998, 39, 2499.
30. (b) Rami, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
31. (c) Li, W.D.; Ma, B.C. Org. Lett. 2005, 7, 271-274.
32. For a compilation of coupling constants reported for all known kinamycins, see the Supporting Information.
33. Furusaki, A.; Matsui, M.; Watanabe, T.; Omura, S.; Nakagawa, A.; Hata, T. Isr. J. Chem. 1972, 10, 173.
34. The literature value is J = 3.4 Hz (ref 1).
35. 3, acetone, and DMSO respectively) (ref 25).
36. Our previous studies of the reactivity of the kinamycins suggest that an intermediate such as 6 would not survive the redox chemistry developed herein for ring D elaboration (refs 4 and 8). The key to the success of this strategy to kinamycin synthesis is the design of a precursor which is compatible with the conditions for ring D elaboration while also being poised for conversion into the delicate diazoquinone functionality that characterizes these interesting natural products.