Cope rearrangement of Δ3,8-taxane tricarbocycles: Remarkable solvent effect on product distribution

Tetrahedron Letters

Volumn 40, Issue 22, 1999, Pages 4235-4238

  Kusama, Hiroyuki ^a   Morihira, Koichiro ^a   Nishimori, Toshiyuki ^a   Nakamura, Takashi ^a   Kuwajima, Isao ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KITASATO INSTITUTE   (Japan)

Author keywords

Dienes; Rearrangements; Solvents and solvent effects; Taxoids

Indexed keywords

CHLOROFORM; METHANOL; SOLVENT; TAXANE DERIVATIVE; TAXOID;

ARTICLE; BIOTRANSFORMATION; CHIRALITY; CYCLIZATION; DRUG TRANSFORMATION; ISOMER; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; THERMOSTABILITY;

EID: 0033612272     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00684-X     Document Type: Article

References (17)

1. a) Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc., 1996, 118, 9186-9187.
2. b) Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc., in press.
3. Morihira, K.; Hara, R.; Kawahara, S.; Nishimori, T.; Nakamura, H.; Kusama, H.; Kuwajima, I. J. Am. Chem. Soc., 1998, 120, 12980-12981.
4. a) Horiguchi, Y.; Furukawa, T.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 8277-8279.
5. b) Furukawa, T.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. Tetrahedron 1992, 48, 6975-6978.
6. c) Seto, M.; Morihira, K.; Katagiri, S.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. Chem. Lett. 1993, 133-136.
7. d) Morihira, K.; Seto, M.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1993, 34, 345-348.
8. e) Nakamura, T.; Waizumi, N.; Tsuruta, K.; Horiguchi, Y.; Kuwajima, I. Synlett 1994, 584-585.
9. f) Seto, M.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. J. Org. Chem. 1994, 59, 3165-3174.
10. On anionic oxy-Cope rearrangement of C9-hydroxy derivative, see Seto, M.; Sakurai, K.; Horiguchi, Y.; Kuwajima, I. Synlett 1994, 993-994.
11. Mukaiyama et. al also found a similar Cope rearrangement of the taxol AB-ring bicyclic system (the compounds 11 and 12 in their previous report; Shiina, I.; Iwadare, H.; Saitoh, M.; Ohkawa, N.; Nishimura, T.; Mukaiyama, T. Chem. Lett. 1995, 781-782), but their reaction was irreversible: private communication.
12. Hill, R. K.; "Cope, oxy-cope and anionic oxy-cope rearrangements" in Comprehensive Organic Synthesis, Trost, B. M. and Fleming, I., Ed., Vol. 5, 785-826, Pergamon Press, Oxford, 1991 and references therein.
13. The taxane numbering system is used throughout.
14. The calculations were performed by using SPARTAN ver 4.1.1 (PM3).
15. Recently, several natural taxanes have been reported to exhibit multi-drug resistance (MDR) reversing activity on cancer cells (Kobayashi J.; Ogiwara A.; Hosoyama H.; Shigemori H.; Yoshida N.; Sasaki T.; Li Y.; Iwasaki S.; Naito M.; Tsuruo T., Tetrahedron, 1994, 50, 7401-7416. Kobayashi J.; Hosoyama H.; Wang X.-x.; Shigemori H.; Koiso Y.; Iwasaki S.; Sasaki T.; Naito M.; Tsuruo T. Bioorg. Med. Chem. Lett., 1997, 7, 393-398.). This prompted us to evaluate such activity of the present spirocyclic compounds. The MDR reversing activity of the derivatives of 4 was evaluated according to the method described in our previous report (Morihira, K.; Nishimori, T.; Kusama, H.; Horiguchi, Y.; Kuwajima, I.; Tsuruo, T. Bioorg. Med. Chem. Lett., 1998, 8, 2173-2176 and 2177-2182.) and was compared with that of verapamil, a well-known MDR reversing agent. Among the several derivatives prepared, the compound 8 was found to exhibit the same potency as verapamil. Thus, the potent activity of 8 clearly shows the possibility of the spirocyclic compounds as a new lead for MDR reversing agents. We are grateful to Professor Takashi Tsuruo (Institute of Molecular and Cellular Biosciences, The University of Tokyo) for the biological assays.
16. Recently, several natural taxanes have been reported to exhibit multi-drug resistance (MDR) reversing activity on cancer cells (Kobayashi J.; Ogiwara A.; Hosoyama H.; Shigemori H.; Yoshida N.; Sasaki T.; Li Y.; Iwasaki S.; Naito M.; Tsuruo T., Tetrahedron, 1994, 50, 7401-7416. Kobayashi J.; Hosoyama H.; Wang X.-x.; Shigemori H.; Koiso Y.; Iwasaki S.; Sasaki T.; Naito M.; Tsuruo T. Bioorg. Med. Chem. Lett., 1997, 7, 393-398.). This prompted us to evaluate such activity of the present spirocyclic compounds. The MDR reversing activity of the derivatives of 4 was evaluated according to the method described in our previous report (Morihira, K.; Nishimori, T.; Kusama, H.; Horiguchi, Y.; Kuwajima, I.; Tsuruo, T. Bioorg. Med. Chem. Lett., 1998, 8, 2173-2176 and 2177-2182.) and was compared with that of verapamil, a well-known MDR reversing agent. Among the several derivatives prepared, the compound 8 was found to exhibit the same potency as verapamil. Thus, the potent activity of 8 clearly shows the possibility of the spirocyclic compounds as a new lead for MDR reversing agents. We are grateful to Professor Takashi Tsuruo (Institute of Molecular and Cellular Biosciences, The University of Tokyo) for the biological assays.
17. Recently, several natural taxanes have been reported to exhibit multi-drug resistance (MDR) reversing activity on cancer cells (Kobayashi J.; Ogiwara A.; Hosoyama H.; Shigemori H.; Yoshida N.; Sasaki T.; Li Y.; Iwasaki S.; Naito M.; Tsuruo T., Tetrahedron, 1994, 50, 7401-7416. Kobayashi J.; Hosoyama H.; Wang X.-x.; Shigemori H.; Koiso Y.; Iwasaki S.; Sasaki T.; Naito M.; Tsuruo T. Bioorg. Med. Chem. Lett., 1997, 7, 393-398.). This prompted us to evaluate such activity of the present spirocyclic compounds. The MDR reversing activity of the derivatives of 4 was evaluated according to the method described in our previous report (Morihira, K.; Nishimori, T.; Kusama, H.; Horiguchi, Y.; Kuwajima, I.; Tsuruo, T. Bioorg. Med. Chem. Lett., 1998, 8, 2173-2176 and 2177-2182.) and was compared with that of verapamil, a well-known MDR reversing agent. Among the several derivatives prepared, the compound 8 was found to exhibit the same potency as verapamil. Thus, the potent activity of 8 clearly shows the possibility of the spirocyclic compounds as a new lead for MDR reversing agents. We are grateful to Professor Takashi Tsuruo (Institute of Molecular and Cellular Biosciences, The University of Tokyo) for the biological assays.