Total synthesis of an enantiomeric pair of FR900482. 3. Completion of the synthesis by assembling the two segments

Tetrahedron

Volumn 53, Issue 30, 1997, Pages 10253-10270

  Katoh, Tadashi ^a   Nagata, Yuriko ^a   Yoshino, Toshiharu ^a   Nakatani, Shogo ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 8ALPHA (CARBAMOYLOXYMETHYL) 3,9 EPOXY 5 FORMYL 1,1A,2,8,9,9A OCTAHYDROAZIRINO[2,3 C][1]BENZAZOCINE 7,9 DIOL ACETATE; 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;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHIRALITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; LEUKEMIA P 388; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

ANIMALIA; MURINAE;

EID: 0030786385     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00652-2     Document Type: Article

References (30)

1. Parts of this series of papers have been the subjects of three preliminary communications: a) Katoh, T., Itoh, E., Yoshino, T., Terashima, S., Tetrahedron Lett., 1996, 37, 3471-3474.
2. b) Yoshino, T., Nagata, Y., Itoh, E., Hashimoto, M., Katoh, T., Terashima, S., ibid., 1996, 37, 3475-3478.
3. c) Katoh, T., Yoshino, T., Nagata, Y., Nakatani, S., Terashima, S., ibid., 1996, 37, 3479-3482.
4. See the reference 2 in the preceding paper (Part 2).
5. Yoshino, T., Nagata, Y., Itoh, E., Hashimoto, M., Katoh, T., Terashima, S., Tetrahedron, the preceding paper (Part 2).
6. Windholz, T. B., Johnston, D. B. R., Tetrahedron Lett., 1967, 2555-2557.
7. Fujii, N., Nakai, K., Habashita, H., Hotta, Y., Tamamura, H., Otaka, A., Ibuka, T., Chem. Pharm. Bull., 1994, 42, 2241-2250.
8. For a recent review of the synthesis and use of chiral aziridines, see, Tanner, D., Angew. Chem. Int. Ed. Engl., 1994, 33, 599-619.
9. Nicolaou, K. C., Webber, S. E., Synthesis, 1986, 453-461.
10. a) Dess, D. B., Martin, J. C., J. Org. Chem., 1983, 48, 4155-4156.
11. b) Dess, D. B., Martin, J. C., J. Am. Chem. Soc., 1991, 113, 7277-7287.
12. c) Ireland, R. E., Liu, L., J. Org. Chem., 1993, 58, 2899.
13. For recent reviews in this field, see, a) Petasis, N. A., Patane, M., A., Tetrahedron, 1992, 48, 5757-5821.
14. b) Rousseau, G., Tetrahedron, 1995, 57, 2777-2849.
15. Since separation of the cyclized product 11 from the unreacted dialdehyde 10 was found to be difficult, the reaction mixture was treated with sodium borohydride at this stage.
16. Details of X-ray crystallographic study will be reported in a separate paper.
17. For a reacent review, see, Hoffman, R., W., Chem. Rev., 1989, 89, 1841-1860.
18. A related base-catalyzed epimerization has been reported for the synthesis of 9-epi-mitomycin B, see, Kasai, M., Kono, M., Shirahata, K., J. Org. Chem., 1989, 54, 5908-5911.
19. 1H-NMR spectra of 17 and i rigorously established identity of their stereostructures. (equation presented)
20. See the reference 10 in the preceding paper (Part 2).
21. Fukuyama, T., Xu, L., Goto, S., J. Am. Chem. Soc., 1992, 114, 383-385.
22. a) Yasuda, N., Williams, R. M., Tetrahedron Lett., 1989, 30, 3397-3400.
23. b) Dmitrienko, G. I., Denhart, D., Mithani, S., Prasad, G. K. B., Taylor, N. J., Tetrahedron Lett., 1992, 33, 5705-5708.
24. Katoh, T., Itoh, E., Yoshino, T., Terashima, S., Tetrahedron, the preceding paper (Part 1).
25. Kiyoto, S., Shibata, T., Yamashita, M., Komori, T., Okuhara, M., Terano, H., Kohsaka, M., Aoki, H., Imanaka, H., J. Antibiot., 1987, 40, 594-599.
26. A related assignment of the C-9 stereochemistries has been reported for the structure determination of FR900482 (1), see, Uchida, I., Takase, S., Kayakiri, H., Kiyoto, S., Hashimoto, M., Tada, T., Koda, S., Morimoto, Y., J. Am. Chem. Soc., 1987, 109, 4108-4109.
27. It has been reported that the cytotoxicity of FK973 against L1210 murine leukemia cells is ca. 10 time more potent than that of FR900482 (1), see, Masuda, K., Suzuki, A., Nakamura, T., Takagi, S., Noda, K., Shinomura, K., Noguchi, H., Shibayama, F., Japan, J., Pharmacol., 1989, 51, 219-226.
28. A mechanistic study on alkylation and cross-linking reaction of DNA by natural mitomycin C and unnatural ent-mitomycin C has been reported, see, Gargiulo, D., Musser, S. S., Yang, L., Fukuyama, T., Tomasz, M., J. Am. Chem. Soc., 1995, 117, 9388-9398.
29. Alley, M. C., Scudiero, D. A.; Monk, A., Hursey, M. L.; Czerwinski, M. J., Fine, D. L.; Abbott, B. L., Mayo, J. G., Shoemaker, R. H., Boyd, M. R., Cancer Res., 1988, 48, 589-594.
30. 1c due to the unexpected technical problems met for measuring an optical rotation.