Synthesis of topostins B567 and D654 (WB-3559D, flavolipin), DNA topoisomerase I inhibitors of bacterial origin

Tetrahedron

Volumn 54, Issue 51, 1998, Pages 15701-15710

  Shioiri, Takayuki ^a   Terao, Yoshihiro ^a   Irako, Naoko ^a   Aoyama, Toyohiko ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Asymmetric reaction; Coupling; Enzyme inhibitors; Topostin

Indexed keywords

BROMIDE; DNA TOPOISOMERASE INHIBITOR; FLAVOLIPIN; LACTOSYLCERAMIDE; RUTHENIUM; TOPOSTIN; UNCLASSIFIED DRUG; WB 3559D;

ACYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROGENATION; MOLECULAR WEIGHT; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032542155     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00984-3     Document Type: Article

References (22)

1. 1. (a) Suzuki, K; Yamaguchi, H.; Miyazaki, S.; Nagai, K.; Watanabe, S.; Saito, T.; Ishii, K.; Hanada, M.; Sekine, T.; Deegami, Y.; Andoh, T. J. Antibiot. 1990, 43, 154.
2. (b) Ikegami, Y.; Takeuchi, N.; Hanada, M.; Hasegawa, Y.; Ishii, K.; Andoh, T.; Sato, T.; Suzuki, K.; Yamaguchi, H.; Miyazaki, S.; Nagai, K.; Watanabe, S.; Saito, T. J. Antibiot. 1990, 43, 158.
3. 2. Private communication from Professor Toshiwo Andoh.
4. 3. (a) Noguchi, H.; Aoyama, T.; Shioiri, T. Tetrahedron 1995, 51, 10531.
5. (b) Noguchi, H.; Aoyama, T.; Shioiri, T.; Tetrahedron 1995, 51, 10545.
6. (c) Fujiwara. H.; Aoyama, T.; Shioiri, T. Tetrahedron 1998, 54, 551.
7. (d) Fujiwara, H.; Egawa, S.; Terao, Y.; Aoyama, T.; Shioiri, T. Tetrahedron 1998, 54, 565.
8. 4. Nemoto, T.; Ojika, M.; Takahata, Y.; Andoh, T.; Sakagami, Y. Tetrahedron 1998, 54, 2683.
9. 5. Kawazoe, R.; Okuyama, H.; Reichardt, W.; Sasaki, S. J. Bacteriol. 1991, 173, 5470.
10. 6. (a) Yoshida, K.; Iwami, M.; Umehara, Y.; Nishikawa, M.; Uchida, I.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1985, 38, 1469.
11. (b) Uchida, I.; Yoshida, K.; Kawai, Y.; Takase, S.; Itoh, Y.; Tanaka, H.; Kohsaka, M.; Imanaka, H. J. Antibiot. 1985, 38, 1476.
12. 7. Shiozalki, M.; Degucji, N.; Mochizuki, T.; Wakabayashi, T.; Ishikawa, T.; Haruyama, H.; Kawai, Y.; Nishijima, M. Tetrahedron in press. We thank Dr. Masao Shiozaki for private communication on the structure of flavolipin.
13. 8. (a) Kamiyama, T.; Umino, T.; Satoh, T.; Sawairi, S.; Shirane, M.; Ohshima, S.; Yokose, K. J. Antibiot. 1995, 48, 924.
14. (b) Kamiyama, T.; Umino, T.; Itezono, Y.; Nakamura, Y.; Satoh, T.; Yokose, K. J. Antibiot. 1995, 48, 929.
15. 9. Kobayashi, J.; Mikami, S.; Shigemori, H.; Takao, T.; Shimonishi, Y.; Izuta, S.; Yoshida, S. Tetrahedron 1995, 51, 10487.
16. 10. (a) We have completed the total synthesis of sulfobacin A : Irako, N.; Shioiri, T. Tetrahedron Lett. 1998, 39, 5793.
17. (b) Sulfobacin B, an analog of sulfobacin A, was also synthesized : Irako, N.; Shioiri, T. Tetrahedron Lett. 1998, 39, 5797.
18. 11. Cf. Brooks, D. W.; Lu, L. D-L.; Masamune, S. Angew. Chem. Int. Ed. Engl. 1979, 18, 72.
19. 12. Cf. Genêt, J.-P.; Ratovelomanana-Vidal, V.; Caño de Andrade, M.C.; Pfister, X.; Guerreiro, P.; Lenoi, J. Y. Tetrahedron Lett.. 1995, 36, 4801.
20. 13. Takuma, S.; Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 3147 and references therein.
21. 14. Grezeszczyk, B.; Konowal, A.; Zamojski, A. Polish J. Chem. 1992, 66, 1627.
22. 15. Ward, D. E.; Rhee, C. K. Tetrahedron Lett. 1991, 32, 7165.