Synthetic study on curacin A: A novel antimitotic agent from the cyanobacterium Lyngbya majuscula

Tetrahedron

Volumn 52, Issue 46, 1996, Pages 14543-14562

  Onoda, Toshihiko ^a   Shirai, Ryuichi ^a   Koiso, Yukiko ^a   Iwasaki, Shigeo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CURACIN A; CYTOTOXIC AGENT;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; MICROTUBULE ASSEMBLY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

LYNGBYA MAJUSCULA; SUIDAE;

EID: 0030580437     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00899-X     Document Type: Article

References (34)

1. 1. For the details on the structures and functions of microtubules, see the following review articles. (a) Dustin, P., Microtubules, Springer-Verlag, New york, 1978.
2. (b) Soifen, D., Ed., Dynamic Aspects of Microtubule Biology, New York Academy of Science, New York, 1986.
3. (c) Avila, J., Ed., Microtubule Proteins, CRC, Boca Raton, FL, 1990.
4. (d) Hamel, E., in Microtubule Proteins, Avila, J., Ed., CRC, Boca Raton, FL, 1990.
5. 2. Iwasaki, S. Med. Res. Rev. 1993, 13, 183-198.
6. 3. Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel, E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994, 59, 1243-1245.
7. 4. Nagle, D. G.; Geralds, R. S.; Yoo, H. -D.; Gerwick, W. H.; Kim, T. -S.; Nambu, M.; White, J. D. Tetrahedron Lett. 1995, 36, 1189-1192.
8. 5. Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1995, 36, 5765-5768.
9. 6. (a) White, J. D.; Kim, T. -S.; Nambu, M. J. Am. Chem. Soc. 1995, 117, 5612-5613.
10. (b) Hoemann, M. Z.; Agrios, K. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 953-956.
11. (c) Ito, H.; Imai, N.; Tanikawa, S.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1795-1798. Ito, H.; Imai, N.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1799-1800.
12. (c) Ito, H.; Imai, N.; Tanikawa, S.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1795-1798. Ito, H.; Imai, N.; Takao, K.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 1799-1800.
13. (d) Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1996, 37, 4397-4400.
14. 7. Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449-8450.
15. 8. Kemp, D. S.; Carey, R. I. J. Org. Chem. 1989, 54, 3640-3646.
16. 9. Duthaler, R. O. Angew. Chem. Int. Ed. Engl. 1991, 30, 705-707 and personal communication.
17. 10. Bergman, R. G. J. Am. Chem. Soc. 1969, 91, 7405-7411.
18. 11. Cabré, J.; Palomo, A. L. Synthesis 1984, 413-417.
19. 12. Takahashi, M.; Iwasaki, S.; Kobayashi, H.; Okuda, S.; Murai, T.; Sato, Y.; Haraguchi-Hiraoka, T.; Nagano, H. J. Antibiotics 1987, 40, 66-72.
20. 13. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321-2336.
21. 14. Onoda, T.; Kawai, N.; Shirai, R.; Iwasaki, S. Tetrahedron in press.
22. 15. (a) Yonetani, K.; Hirotsu, T.; Shiba, T. Bull. Chem. Soc. Jpn. 1975, 48, 3302-3305.
23. (b) Hirotsu, Y.; Shiba, T.; Kaneko, T. Bull. Chem. Soc. Jpn. 1967, 40, 2945-2949.
24. 16. Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. J. Org. Chem. 1982, 47, 2670-2673.
25. 17. Kocienski, P. J.; Cernigliaro, G.; Feldstein, G. J. Org. Chem. 1977, 42, 353-355.
26. 18. Yao, Z. -J.; Wu, Y. -L. J. Org. Chem. 1995, 60, 1170-1176.
27. 19. Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron 1967, 23, 2709-2720.
28. 20. Takeda, K.; Kobayashi, T.; Saito, K.; Yoshii, E. J. Org. Chem. 1988, 53, 1092-1095.
29. 21. Yan, L.; Kahne, D. Synlett 1995, 523-524.
30. 22. (a) Tsuji, T.; Kataoka, T.; Yoshioka, M.; Sendo, Y.; Nishitani, Y.; Hirai, S.; Maeda, T.; Nagata, W. Tetrahedron Lett. 1979, 30, 2793-2796.
31. (b) Fuji, K.; Ichikawa, K.; Node, M.; Fujita, E. J. Org. Chem. 1979, 44, 1661-1664.
32. See also, (c) Akiyama, T.; Shima, H.; Ozaki, S. Synlett 1992, 415-416.
33. (d) Akiyama, T.; Hirofuji, H.; Ozaki, S. Tetrahedron Lett. 1991, 32, 1321-1324.
34. 23. Onoda, T.; Shirai, R.; Iwasaki, S. unpublished results.