Total Synthesis of Natural (−)-Ptaquilosin, the Aglycon of a Potent Bracken Carcinogen Ptaquiloside, and the (+)-Enantiomer and Their DNA Cleaving Activities

Journal of the American Chemical Society

Volumn 115, Issue 8, 1993, Pages 3056-3065

  Kigoshi, Hideo ^a   Imamura, Yoshifumi ^a   Mizuta, Kazuhiro ^a   Niwa, Haruki ^a   Yamada, Kiyoyuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001290250     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00061a003     Document Type: Article

References (29)

1. Evans, I. A. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; American Chemical Society: Washington, DC, 1984; Vol. 2, pp 1171–1204.
2. Hirono, I.; Yamada, K. In Naturally Occurring Carcinogens of Plant Origin; Hirono, I., Ed.; Kodansha-Elsevier: Tokyo-Amsterdam, 1987; pp 87–120.
3. Niwa, H.; Ojika, M.; Wakamatsu, K.; Yamada, K.; Hirono, I.; Matsushita, K. Tetrahedron Lett. 1983, 24, 4117–4120.
4. Niwa, H.; Ojika, M.; Wakamatsu, K.; Yamada, K.; Ohba, S.; Saito, Y.; Hirono, I.; Matsushita, K. Tetrahedron Lett. 1983, 24, 5371–5372.
5. Ohba, S.; Saito, Y.; Hirono, I.; Niwa, H.; Ojika, M.; Wakamatsu, K.; Yamada, K. Acta Crystallogr., Sect. C 1984, 40, 1877–1879.
6. Ojika, M.; Wakamatsu, K.; Niwa, H.; Yamada, K. Tetrahedron 1987, 43, 5261–5274.
7. Hirono, I.; Yamada, K.; Niwa, H.; Shizuri, Y.; Ojika, M.; Hosaka, S.; Yamaji, T.; Wakamatsu, K.; Kigoshi, H.; Niiyama, K.; Uosaki, Y. Cancer Lett. 1984, 21, 239–246.
8. Hirono, I.; Aiso, S.; Yamaji, T.; Mori, H.; Yamada, K.; Niwa, H.; Ojika, M.; Wakamatsu, K.; Kigoshi, H.; Niiyama, K.; Uosaki, Y. Gann 1984, 75, 833–836.
9. Hirono, I.; Ogino, H.; Fujimoto, M.; Yamada, K.; Yoshida, Y.; Ikagawa, M.; Okumura, M. J. Natl. Cancer Inst. 1987, 79, 1143–1146.
10. Ojika, M.; Sugimoto, K.; Okazaki, T.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1775–1777.
11. Kigoshi, H.; Sawada, A.; Nakayama, Y.; Niwa, H.; Yamada, K. Tetrahedron Lett. 1989, 30, 1983–1986.
12. Kigoshi, H.; Imamura, Y.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1989, 111, 2302–2303.
13. Misumi, A.; Iwanaga, K.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 3343–3345.
14. Furuta, K.; Iwanaga, K.; Yamamoto, H. Org. Synth. 1988, 67, 76–85.
15. Naef, R.; Seebach, D. Angew. Chem, Int. Ed. Engl. 1981, 20, 1030–1031.
16. Ladner, W. Angew. Chem., Int. Ed. Engl. 1982, 21, 449–450.
17. Ladner, W. Chem. Ber. 1983, 116, 3413.
18. Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194–1216.
19. Kigoshi, H.; Imamura, Y.; Yoshikawa, K.; Niwa, H.; Yamada, K. Tetrahedron Lett. 1991, 32, 4541–4544.
20. Ho, T.-L. Hard and Soft Acids and Bases Principle in Organic Chemistry; Academic Press: New York, 1977.
21. Kim, S.; Lhim, D. C. Bull. Chem. Soc. Jpn. 1986, 59, 3297–3298.
22. Ruder, S. M.; Ronald, R. C. Tetrahedron Lett. 1984, 25, 5501–5504.
23. Yates, P.; Helferty, P. H.; Mahler, P. Can. J. Chem. 1983, 61, 78–85.
24. Newman, M. S.; DeVries, J.; Darlak, R. J. Org. Chem. 1966, 31, 2171–2174.
25. Kigoshi, H.; Sawada, A.; Nakayama, Y.; Niwa, H.; Yamada, K. Tetrahedron Lett. 1989, 50, 1983–1986.
26. Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Mizuta, K.; Yamada, K. Tetrahedron Lett. 1992, 33, 6647–6650.
27. Noyori, R.; Nishida, I.; Sakata, J. Tetrahedron Lett. 1980, 21, 2085–2088.
28. Kigoshi, H.; Imamura, Y.; Sawada, A.; Niwa, H.; Yamada, K. Bull. Chem. Soc. Jpn. 1991, 64, 3735–3737.
29. Kigoshi, H.; Sawada, A.; Imamura, Y.; Niwa, H.; Yamada, K. Tetrahedron 1989, 45, 2551–2556.