Synthesis of the first photo-triggered pro-mitosene based on FR-900482

Tetrahedron

Volumn 56, Issue 4, 2000, Pages 521-532

  Williams, Robert M ^a   Rollins, Samuel B ^a   Judd, Ted C ^a  

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

Author keywords

Antitumor antibiotic; Aziridine; FR 900482; Mitosene; Photochemical trigger

Indexed keywords

4 FORMYL 6,9 DIHYDROXY 14 OXA 1,11 DIAZATETRACYCLO[7.4.1.0 2,7 0 10,12]TETRADECA 2,4,6 TRIEN 8 YLMETHYLCARBAMATE; ANTINEOPLASTIC ANTIBIOTIC; MITOSENE; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0034695672     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01046-7     Document Type: Article

References (50)

1. (a) Iwami, M.; Kiyoto, S.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiotics 1987, 40, 589-593.
2. (b) Kiyoto, S.; Shibata, T.; Yamashita, M.; Komori, T.; Okuhara, M.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiotics 1987, 40, 594-599.
3. (c) Uchida, I.; Takase, S.; Kayakiri, H.; Kiyoto, S.; Hashimoto, M.; Tada, T.; Koda, S.; Morimoto, Y. J. Am. Chem. Soc. 1987, 109, 4108-4109.
4. (a) Shimomura, K.; Hirai, O.; Mizota, T.; Matsumoto, S.; Mori, J.; Shibayama, F.; Kikuchi, H. J. Antibiotics 1987, 40, 600-606.
5. (b) Hirai, O.; Shimomura, K.; Mizota, T.; Matsumoto, S.; Mori, J.; Kikuchi, H. J. Antibiotics 1987, 40, 607-611.
6. Terano H., Takase S., Hosoda J., Kohsaka M. J. Antibiotics. 42:1989;145-148.
7. (a) Shimomura, K.; Manda, T.; Mukumoto, S.; Masuda, K.; Nakamura, T.; Mizota, T.; Matsumoto, S.; Nishigaki, F.; Oku, T.; Mori, J.; Shibayama, F. Cancer Res. 1988, 48, 1166-1172.
8. (b) Nakamura, T.; Masuda, K.; Matsumoto, S.; Oku, T.; Manda, T.; Mori, J.; Shimomura, K. Jpn. J. Pharmacol. 1989, 49, 317-324.
9. (a) Naoe, Y.; Inami, M.; Matsumoto, S.; Nishigaki, F.; Tsujimoto, S.; Kawamura, I.; Miyayasu, K.; Manda, T.; Shimomura, K. Cancer Chemother. Pharmacol. 1998, 42, 31-36.
10. (b) Naoe, Y.; Inami, M.; Kawamura, I.; Nishigaki, F.; Tsujimoto, S.; Matsumoto, S.; Manda, T.; Shimomura, K. Jpn. J. Cancer Res. 1998, 89, 666-672.
11. (c) Naoe, Y.; Inami, M.; Takagaki, S.; Matsumoto, S.; Kawamura, I.; Nishigaki, F.; Tsujimoto, S.; Manda, T.; Shimomura, K. Jpn. J. Cancer Res. 1998, 89, 1047-1054.
12. (d) Naoe, Y.; Inami, M.; Matsumoto, S.; Takagaki, S.; Fujiwara, T.; Yamazaki, S.; Kawamura, I.; Nishigaki, F.; Tsujimoto, S.; Manda, T.; Shimomura, K. Jpn. J. Cancer Res. 1998, 89, 1306-1317.
13. (e) Naoe, Y.; Kawamura, I.; Inami, M.; Matsumoto, S.; Nishigaki, F.; Tsujimoto, S.; Manda, T.; Shimomura, K. Jpn. J. Cancer Res. 1998, 89, 1318-1325.
14. (a) Masuda, K.; Nakamura, T.; Mizota, T.; Mori, J.; Shimomura, K. Cancer Res. 1988, 48, 5172-5177.
15. (b) Masuda, K.; Nakamura, T.; Shimomura, K. J. Antibiotics 1988, 41, 1497-1499.
16. (a) Williams, R. M.; Rajski, S. R. Tetrahedron Lett. 1992, 33, 2929-2932.
17. (b) Williams, R. M.; Rajski, S. R. Tetrahedron Lett. 1993, 34, 7023-7026.
18. (c) Huang, H.; Rajski, S. R.; Williams, R. M.; Hopkins, P. B. Tetrahedron Lett. 1994, 35, 9669-9672.
19. (d) Williams, R. M.; Rajski, S. R. Chem. Biol. 1997, 4, 127-137.
20. (e) Williams, R. M.; Rajski, S. R. J. Am. Chem. Soc. 1998, 120, 2192-2193.
21. (a) Woo, J.; Sigurdsson, S. T.; Hopkins, P. B. J. Am. Chem. Soc. 1993, 115, 1199-1200.
22. (b) Huang, H.; Pratum, T. K.; Hopkins, P. B. J. Am. Chem. Soc. 1994, 116, 2703-2709.
23. (c) Paz, M. M.; Hopkins, P. B. Tetrahedron Lett. 1997, 38, 343-346.
24. (d) Paz, M. M.; Hopkins, P. B. J. Am. Chem. Soc. 1997, 119, 5999-6005.
25. (a) Tomasz, M.; Lipman, R.; Chowdary, D.; Pawlak, J.; Verdine, G.; Nakanishi, K. Science 1987, 235, 1204-1208.
26. (b) Tomasz, M. Chem. Biol. 1995, 2, 575-579 and references cited therein.
27. Rajski S.R., Williams R.M. Chem. Rev. 98:1998;2723-2796.
28. Fukuyama T., Goto S. Tetrahedron Lett. 30:1989;6491-6494.
29. (a) Yasuda, N.; Williams, R. M. Tetrahedron Lett. 1989, 30, 3397-3400.
30. (b) Jones, R. J.; Rapoport, H. J. Org. Chem. 1990, 55, 1144-1146.
31. (c) Martin, S. F.; Wagman, A. S. Tetrahedron Lett. 1995, 36, 1169-1170.
32. (d) Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108-2109.
33. (e) Lim, H.-J.; Sulikowski, G. A. Tetrahedron Lett. 1996, 37, 5243-5246.
34. (f) Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083-1094.
35. (g) Mithani, S.; Drew, D. M.; Rydberg, E. H.; Taylor, N. J.; Mooibroek, S.; Dmitrienko, G. I. J. Am. Chem. Soc. 1997, 119, 1159-1160.
36. (a) Fukuyama, T.; Xu, L.; Goto, S.; J. Am. Chem. Soc. 1992, 114, 383-385.
37. (b) Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722-4723.
38. (c) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S.; Tetrahedron Lett. 1996, 37, 3471-3474.
39. (d) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
40. (e) Katoh, T.; Yoshino, T.; Nagata, Y.; Nakatani, S.; Terashima, S. Tetrahedron Lett. 1996, 37, 3479-3482.
41. This work was reported in a preliminary communication, see: Rollins, S. B.; Williams, R. M. Tetrahedron Lett. 1997, 38 4033-4036.
42. Spada M.R., Ubukata M., Isono K. Heterocycles. 34:1992;1147-1151.
43. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
44. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
45. (c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
46. Nielson O.B.T., Bruun H., Bretting C., Feit P.W. J. Med. Chem. 18:1975;41-50.
47. Pillai V.N.R. Synthesis. 1980;1-26.
48. 2O at room temperature led to no detectable loss of the starting material
49. From this point forward, only the major diastereomer series was carried through.
50. The stereochemistry of tetraacetates i and ii has previously been determined: Egbertson, M. S. PhD Dissertation, Yale University, 1989.