Synthetic studies on FR 900482. Synthesis of a photo-triggered pro-mitosene

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4033-4036

  Rollins, Samuel B ^a   Williams, Robert M ^a  

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

Author keywords

[No Author keywords available]

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; PRODRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0030908763     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00865-4     Document Type: Article

References (39)

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. 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, 1989, 42, 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. Japan. J. Pharmacol., 1989, 49, 317-324.
9. a) Masuda, K.; Nakamura, T.; Mizota, T.; Mori, J.; Shimomura, K. Cancer Res., 1988, 48, 5172-5177;
10. b) Masuda, K.; Nakamura, T.; Shimomura, K. J. Antibiotics, 1988, 41, 1497-1499.
11. a) Williams, R. M.; Rajski, S. R. Tetrahedron Lett. 1993, 34, 7023-7026;
12. b) Huang, H; Pratum, T. K.; Hopkins, P. B. J. Am. Chem. Soc. 1994, 116, 2703-2709;
13. Williams, R. M.; Rajski, S. R. Tetrahedron Lett. 1992, 33, 2929-2932;
14. Woo, J.; Sigurdsson, S. T.; Hopkins, P. B., J. Am. Chem. Soc. 1993, 115, 1199-1200;
15. e) Huang, H.; Rajski, S. R.; Williams, R. M.; Hopkins, P. B., Tetrahedron Lett.,1994, 35, 9669-9672;
16. f) Paz, M.M.; Hopkins, P. B., Tetrahedron Lett. 1997, 38, 343-346;
17. g) Williams, R. M.; Rajski, S. R., Chem. & Biol., 1997, 4, 127.
18. Fukuyama, T.; Goto, S. Tetrahedron Lett., 1989, 30, 6491-6494.
19. a) Tomasz, M; Lipman, R.; Chowdary, D.; Pawlak, J.; Verdine, G.; Nakanishi, K., Science, 1987, 235, 1204;
20. b) Tomasz, M., Chem. & Biol. 1995, 2, 575 and references cited therein.
21. a) Yasuda, N.; Williams, R. M. Tetrahedron Lett., 1989, 30, 3397-3400;
22. b) Jones, R. J.; Rapoport, H., J. Org. Chem., 1990, 55, 1144-1146;
23. Martin, S. F.; Wagman, A. S., Tetrahedron Lett., 1995, 36, 1169-1170;
24. Miller, S.J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H., J. Am. Chem. Soc., 1995, 117, 2108-2109;
25. e) Lim, H.-J.; Sulikowski, G. A.; Tetrahedron Lett., 1996, 37, 5243-5246;
26. f) Ziegler, F. E.; Belema, M.;J. Org. Chem., 1997, 62, 1083-1094;
27. 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.
28. a) Fukuyama, T.; Xu, L.; Goto, S., J. Am. Chem. Soc., 1992, 114, 383-385;
29. b) Schkeryantz, J. M.; Danishefsky, S. J., J. Am. Chem. Soc., 1995, 117, 4722-4723;
30. Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S., Tetrahedron Lett., 1996, 37, 3471-3474;
31. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S., Tetrahedron Lett., 1996, 37, 3475-3478;
32. e) Katoh, T.; Yoshino, T.; Nagata, Y.; Nakatani, S.; Terashima, S., Tetrahedron Lett.,1996, 37, 3479-3482.
33. a) Dess, D. B.; Martin, J. C., J. Org. Chem., 1983, 48, 4155-4156;
34. b) Dess, D. B.; Martin, J. C., J. Am. Chem. Soc., 1991, 113, 7277-7287;
35. Ireland, R. E.; Liu, L., J. Org. Chem.., 1993, 58, 2899.
36. Nielson, O. B. T.; Bruun, H.; Bretting, C.; Feit, P. W., J. Med. Chem., 1975, 18, 41-50.
37. Pillai, V. N. R., Synthesis, 1980, 1-26.
38. 2O at room temperature led to no detectable loss of the starting material.
39. 13C nmr, ir, mass spectrum and / or combustion analytical data consistent with the assigned structures.