The total synthesis of dynemicin A leading to development of a fully contained bioreductively activated enediyne prodrug

Journal of the American Chemical Society

Volumn 118, Issue 40, 1996, Pages 9509-9525

  Shair, Matthew D ^a,b,c,d   Yoon, Tae Young ^a,c   Mosny, Karoline K ^c   Chou, T C ^c   Danishefsky, Samuel J ^a,b,c  

^a YALE UNIVERSITY   (United States)

^b Columbia University ^*  (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^d HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; DYNEMICIN A; MITOMYCIN C;

ADENOCARCINOMA; ANIMAL CELL; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DNA CLEAVAGE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MOUSE; NONHUMAN; REACTION ANALYSIS; TECHNIQUE; TUMOR CELL;

EID: 0030001543     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960040w     Document Type: Article

References (61)

1. Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyaki, T.; Oki, T.; Kawaguchi, H.; VanDuyne, G. D.; Clardy, J. J. Antibiot. 1989, 42, 1449.
2. Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3715.
3. For a personalized retrospective treatment of the biology and chemistry of the enediyne antibiotics, see: (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem., 1996, 61, 16.
4. (b) See, also: Yoon, T. Y. Ph.D. Thesis, Yale University, 1994.
5. (b) Enediyne Antibiotics as Antitumor Agents; Doyle, T. W., Borders, D. B., Eds.; Marcel-Decker: New York, 1994.
6. (c) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
7. (a) Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chane, C. C.; Morton, G. O.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3454.
8. (b) Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chang, C. C.; Morton, G. O.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466.
9. (c) Zein, N.; Sinha, A.; McGahren, W. J.; Ellestad, G. A. Science 1988, 240, 1198.
10. (d) Casazza, A. M.; Kelley, S. L. Biological Properties of Esperamicin and Other Enediyne Antibiotics. In Enediyne Antibiotics as Antitumor Agents; Doyle, T. W., Borders, D. B., Eds., Marcel-Dekker: New York, 1994; pp 283-299.
11. (a) Golik, J.; Clardy, J.; Dubay, G.; Groenwold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkum, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3461.
12. (b) Golik, J.; Clardy, J.; Dubay, G.; Groenwold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkum, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462.
13. Sugiura, Y.; Shiraki, T.; Konishi, M.; Oki, T. Proc. Natl. Acad. Sci. U. S.A. 1990, 87, 3831.
14. Langley, D. R.; Doyle, T. W.; Beveridge, D. L. J. Am. Chem. Soc. 1991, 113, 4395.
15. Wender, P. A.; Kelly, R. C.; Beckham, S.; Miller, B. L. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 8835.
16. Sugiura, Y.; Shiraki, T. Biochemistry 1990, 29, 9795.
17. For insight into the dynamics of dynemicin-DNA interactions, see: Myers, A. G.; Cohen, S. B.; Tom, N. J.; Madar, D. J.; Fraley, M. E. J. Am. Chem. Soc. 1995, 117, 7574.
18. Semmelhack, M. F.; Gallagher, J.; Cohen, D. Tetrahedron Lett. 1990, 31, 1521.
19. For synthesis of various dynemicin A model systems, see: (a) Nicolaou, K. C.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 8908 and references cited therein.
20. (b) Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E.-M. J. Org. Chem. 1993, 58, 5867 and references cited therein.
21. (c) Nishigawa, T.; Isobe, M.; Goto, T. Synlett 1991, 393.
22. (d) Magnus, P.; Font, S. M. J. Chem. Soc., Chem. Commun. 1991, 544.
23. (e) Takahashi, T.; Sakamoto, Y.; Yamada, H.; Usui, S.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1995, 34, 1345.
24. (f) Nicolaou, K. C.; Dai, W.-M.; Tsay, S.-C.; Estevez, V. A.; Wrasildo, W. Science 1992, 256, 1172.
25. (a) Porco, J. A., Jr.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410.
26. (b) Wood, J. L.; Porco, J. A., Jr.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898.
27. Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378.
28. Myers, A. G.; Fraley, M. E.; Tom. N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33.
29. For a recent review of the chemsitry and biomechanistics of the mitomycins, see: Schkerynatz, J.; Danishefsky, S. J. Synlett #5, 1995, 475.
30. (a) Shair, M. D.; Yoon, T. Y.; Chou, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477.
31. (b) Shair, M. D. Ph.D. Thesis, Columbia University, 1995.
32. Shair, M. D.; Yoon, T. Y.; Chou, D.; Danishefsky, S. J. Patent Application 08/347, 952.
33. Chou, D.; Shair, M. D.; Yoon, T. Y.; Zheng, Y. H.; Danishefsky, S. J. Proc. Am. Assoc. Cancer Res. 1995, 36: 384.
34. Shair, M. D.; Yoon, T. Y.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1721.
35. Popp, F. D. Chem. Heterocycl. Comp. 1982, 32, 353 and references cited therein.
36. Yoon, T. Y.; Shair, M. D.; Danishefsky, S. J.; Schulte, G. K. J. Org. Chem. 1994, 59, 3752.
37. Taken in part from the following: Yoon, T. Y. Ph.D. Thesis, Yale University, 1994.
38. Yoon, T. Y.; Shair, M. D.; Danishefsky, S. J. Tetrahedron Lett. 1994, 35, 6259.
39. Lakshman, M. K.; Sayer, J. M.; Jerina, D. M. J. Am. Chem. Soc. 1991, 113, 6589.
40. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1979, 44, 4148.
41. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.
42. Four, P.; Guibe, F. Tetrahedron Lett. 1982, 23, 1825.
43. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
44. For the only example of this type of construction to produce a cyclic enediyne in the context of an annulene synthesis, see: Huynh, C.; Linstrumelle, G. Tetrahedron 1988, 44, 6337.
45. Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138.
46. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
47. Nicolaou, K. C.; Chakraborty, T. Y.; Piscopio, A. D.; Monowa, N; Bertinato, P. J. Am. Chem. Soc. 1993, 115 4419.
48. (a) Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, R. Angew. Chem., Int Ed. Engl. 1984, 23, 727.
49. (b) Mitchell, T. N.; Amamria, A.; Killing, H.; Rutschow, D. J. Organomet. Chem. 1986, 304, 257.
50. Shair, M. D.; Yoon, T. Y.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 3755.
51. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
52. Hanson, J. R. Synthesis 1974, 1.
53. Tirpak, R. E.; Olsen, R. S.; Rathke, M. W. J. Org. Chem. 1985, 50, 4877.
54. For an excellent survey of methods to construct anthraquinone constructs, see: Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790.
55. Tamura, Y.; Fukata, F.; Sasho, M.; Tsugoshi, T.; Kita, Y. J. Org. Chem. 1985, 50, 2273 and references cited therein.
56. Guyot, M.; Molho, D. Tetrahedron Lett. 1973, 14, 3433.
57. Kita, Y.; Akai, S.; Ajimura, N.; Yoshigi, M.; Yasuda, H.; Tamura, Y. J. Org. Chem. 1986, 51, 4150.
58. 1H NMR spectrum matched well with a related model system.
59. For the conversion of anthracenols to anthraquinones in the presence of ground state oxygen and light, see: (a) Cameron, D. W.; Schultz, P. E. J. Chem. Soc. (C) 1967, 2121.
60. (b) Julian, P. L.; Cole, G. J. Am. Chem. Soc. 1945, 67, 1721.
61. Nicolaou, K. C.; Maligres, P.; Suzuki, T.; Wendeborn, W. V.; Dai, W.-M.; Chadha, R. K. J. Am. Chem. Soc. 1992, 114, 8890.