Total synthesis of natural (+)-FR900482. 3. Completion of the synthesis

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3479-3482

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

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

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; ANTINEOPLASTIC AGENT;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030001093     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00595-3     Document Type: Article

References (22)

1. See the reference 1 in the preceding paper.
2. Yoshino, T., Nagata, Y., Itoh, E., Hashimoto, M., Katoh, T., Terashima, S., Tetrahedron Lett., the preceding paper.
3. Windholz, T. B., Johnston, D. B. R., Tetrahedron Lett., 1967, 2555-2557.
4. Fujii, N., Nakai, K., Habashita, H., Hotta, Y., Tamamura, H., Otaka, A., Ibuka, T., Chem. Pharm. Bull., 1994, 42, 2241-2250.
5. For a recent review of the synthesis and use of chiral aziridines, see, Tanner, D., Angew. Chem. Int. Ed. Engl., 1994, 33, 599-619.
6. Nicolaou, K. C., Webber, S. E., Synthesis, 1986, 453-461.
7. a) Dess, D. B., Martin, J. C., J. Org. Chem., 1983, 48, 4155-4156.
8. b) Dess, D. B., Martin, J. C., J. Am. Chem. Soc., 1991, 113, 7277-7287.
9. c) Ireland, R. E., Liu, L., J. Org. Chem., 1993, 58, 2899.
10. Detailed discussions on the mechanism of the intramolecular aldol reaction will be presented in a full account.
11. To be published in a separate paper.
12. 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.
13. Prolonged reaction times caused dehydration of both 14 and 15 to produce the same exocyclic enone.
14. When silyl ether 13 was employed as the substrate for the epimerization, none of the emiperized product was isolated, but the same enone as obtained from both 14 and 15 was produced by elimination of the siloxy moiety (see, ref. 11) in an almost quantitative yield.
15. See the reference 9 in the preceding paper.
16. Fukuyama, T., Xu, L., Goto, S., J. Am. Chem. Soc., 1992, 114, 383-385.
17. a) Yasuda, N., Williams, R. M., Tetrahedron Lett., 1989, 30, 3397-3400.
18. b) Dmitrienko, G. I., Denhart, D., Mithani, S., Prasad, G. K. B., Taylor, N. J., Tetrahedron Lett., 1992, 33. 5705-5708.
19. 1H-NMR spectrum. A related assignment of the C-8 stereochemistries has been reported for the structure determination of 1, see, Uchida, I., Takase, S., Kayakiri, H., Kiyoto, S., Hashimoto, M., Tada, T., Koda, S., Morimoto, Y., J. Am. Chem. Soc., 1987, 40, 4108-4109.
20. Katoh, T., Itoh, E., Yoshino, T., Terashima, S., Tetrahedron Lett., the preceding paper.
21. Kiyoto, S., Shibata, T., Yamashita, M., Komori, T., Okuhara, M., Terano, H., Kohsaka, M., Aoki, H., Imanaka, H., J. Antibiot., 1987, 40, 594-599.
22. This compound was further converted to the triacetyl derivative, which was identical with an authentic sample of FK973.