Wagner-Meerwein rearrangement of duocarmycins

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 5, 1996, Pages 933-939

  Nagamura, Satoru ^a,c   Kanda, Yutaka ^a   Asai, Akira ^a   Kobayashi, Eiji ^b   Gomi, Katsushige ^b   Saito, Hiromitsu ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

^b Pharmaceutical Research Laboratories   (Japan)

^c NONE   (Japan)

Author keywords

anticellular activity; carbamoylderivative; duocarmycin; spiro compound; Wagner Meerwein rearrangement

Indexed keywords

CAMPHOR; DUOCARMYCIN B2; SULFONIC ACID DERIVATIVE; TOLUENE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR INTERACTION;

EID: 0029974874     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.933     Document Type: Article

References (32)

1. a) Takahashi I., Takahashi K., Ichimura M., Morimoto M., Asano K., Kawamoto I., Tomita F., Nakano H., J. Antibiot., 41, 1915-1917 (1988);
2. b) Ichimura M., Muroi K., Asano K., Kawamoto I., Tomita F., Morimoto M., Nakano H., ibid., 41, 1285-1288 (1988);
3. c) Ogawa T., Ichimura M., Katsumata S., Morimoto M., Takahashi K., ibid., 42, 1299-1301 (1989);
4. d) Ichimura M., Ogawa T., Takahashi K., Kobayashi E., Kawamoto I., Yasuzawa T., Takahashi I., Nakano H., ibid., 43, 1037-1038 (1990);
5. e) Ichimura M., Ogawa T., Katsumata S., Takahashi K., Takahashi I., Nakano H., ibid., 44, 1045-1053 (1991).
6. Yasuzawa T., Iida T., Muroi K., Ichimura M., Takahashi K., Sano H., Chem. Pharm. Bull., 36, 3728-3731 (1988); Yasuzawa T., Saitoh Y., Ichimura M., Takahashi I., Sano H., J. Antibiot., 44, 445-447 (1991).
7. Yasuzawa T., Iida T., Muroi K., Ichimura M., Takahashi K., Sano H., Chem. Pharm. Bull., 36, 3728-3731 (1988); Yasuzawa T., Saitoh Y., Ichimura M., Takahashi I., Sano H., J. Antibiot., 44, 445-447 (1991).
8. Hanka L. J., Dietz A., Gerpheide S. A., Kuentzel S. L., Martin D. G., J. Antibiot., 31, 1211-1217 (1978); Martin D. G., Chidester C. G., Duchamp D. J., Mizsak S. A., ibid., 33, 902-903 (1980); Chidester C. G., Krueger W. C., Mizsak S. A., Duchamp D. J., Martin D. G., J. Am. Chem. Soc., 103, 7629-7635 (1981); Hurley L. H., Reynolds V. L., Swenson D. H., Petzold G. L., Scahill T. A., Science, 226, 843-844 (1984).
9. Hanka L. J., Dietz A., Gerpheide S. A., Kuentzel S. L., Martin D. G., J. Antibiot., 31, 1211-1217 (1978); Martin D. G., Chidester C. G., Duchamp D. J., Mizsak S. A., ibid., 33, 902-903 (1980); Chidester C. G., Krueger W. C., Mizsak S. A., Duchamp D. J., Martin D. G., J. Am. Chem. Soc., 103, 7629-7635 (1981); Hurley L. H., Reynolds V. L., Swenson D. H., Petzold G. L., Scahill T. A., Science, 226, 843-844 (1984).
10. Hanka L. J., Dietz A., Gerpheide S. A., Kuentzel S. L., Martin D. G., J. Antibiot., 31, 1211-1217 (1978); Martin D. G., Chidester C. G., Duchamp D. J., Mizsak S. A., ibid., 33, 902-903 (1980); Chidester C. G., Krueger W. C., Mizsak S. A., Duchamp D. J., Martin D. G., J. Am. Chem. Soc., 103, 7629-7635 (1981); Hurley L. H., Reynolds V. L., Swenson D. H., Petzold G. L., Scahill T. A., Science, 226, 843-844 (1984).
11. Hanka L. J., Dietz A., Gerpheide S. A., Kuentzel S. L., Martin D. G., J. Antibiot., 31, 1211-1217 (1978); Martin D. G., Chidester C. G., Duchamp D. J., Mizsak S. A., ibid., 33, 902-903 (1980); Chidester C. G., Krueger W. C., Mizsak S. A., Duchamp D. J., Martin D. G., J. Am. Chem. Soc., 103, 7629-7635 (1981); Hurley L. H., Reynolds V. L., Swenson D. H., Petzold G. L., Scahill T. A., Science, 226, 843-844 (1984).
12. Sugiyama H., Hosoda M., Saito I., Asai A., Saito H., Tetrahedron Lett., 31, 7197-7200 (1990); Sugiyama H., Ohmori K., Chan K. L., Hosoda M., Asai A., Saito H., Saito I, ibid., 34, 2179-2182 (1993); Boger D. L., Ishizaki T., Zarrinmayeh H., J. Am. Chem. Soc., 113, 6645-6649 (1991).
13. Sugiyama H., Hosoda M., Saito I., Asai A., Saito H., Tetrahedron Lett., 31, 7197-7200 (1990); Sugiyama H., Ohmori K., Chan K. L., Hosoda M., Asai A., Saito H., Saito I, ibid., 34, 2179-2182 (1993); Boger D. L., Ishizaki T., Zarrinmayeh H., J. Am. Chem. Soc., 113, 6645-6649 (1991).
14. Sugiyama H., Hosoda M., Saito I., Asai A., Saito H., Tetrahedron Lett., 31, 7197-7200 (1990); Sugiyama H., Ohmori K., Chan K. L., Hosoda M., Asai A., Saito H., Saito I, ibid., 34, 2179-2182 (1993); Boger D. L., Ishizaki T., Zarrinmayeh H., J. Am. Chem. Soc., 113, 6645-6649 (1991).
15. Hurley L. H., Reynolds V. L., Swenson D. H., Petzold G. L., Scahill T. A., Science, 226, 843-844 (1984); Raynolds V. L., Molineaux I. J., Kaplan D. J., Swensen D. H., Hurley L. H., Biochemistry, 24, 6228-6237 (1985); Tang M. S., Lee C. S., Doisy R., Ross L., Needham-VanDevanter D. R., Hurley L. H., ibid., 27, 893-901 (1988).
16. Hurley L. H., Reynolds V. L., Swenson D. H., Petzold G. L., Scahill T. A., Science, 226, 843-844 (1984); Raynolds V. L., Molineaux I. J., Kaplan D. J., Swensen D. H., Hurley L. H., Biochemistry, 24, 6228-6237 (1985); Tang M. S., Lee C. S., Doisy R., Ross L., Needham-VanDevanter D. R., Hurley L. H., ibid., 27, 893-901 (1988).
17. Hurley L. H., Reynolds V. L., Swenson D. H., Petzold G. L., Scahill T. A., Science, 226, 843-844 (1984); Raynolds V. L., Molineaux I. J., Kaplan D. J., Swensen D. H., Hurley L. H., Biochemistry, 24, 6228-6237 (1985); Tang M. S., Lee C. S., Doisy R., Ross L., Needham-VanDevanter D. R., Hurley L. H., ibid., 27, 893-901 (1988).
18. a) Nagamura S., Kanda Y., Kobayashi E., Gomi K., Saito H., Chem. Pharm. Bull., 43, 1530-1535 (1995);
19. b) Gomi K., Kobayashi E., Miyoshi K., Ashizawa T., Okamoto A., Ogawa T., Katsumata S., Mihara A., Okabe M., Hirata T., Jpn. J. Cancer Res. (Gann), 83, 113-120 (1992).
20. Nagamura S., Asai A., Kanda Y., Kobayashi E., Gomi K., Saito H., submitted for publication.
21. Yasuzawa T., Muroi K., Ichimura M., Takahashi I., Ogawa T., Takahashi K., Sano H., Saitoh Y., Chem. Pharm. Bull., 43, 378-391 (1995).
22. Berner D., Cox D. P., Dahn H., J. Am. Chem. Soc., 104, 2631-2632 (1982); Abe Y., Suehiro T., Chem. Lett., 1982, 337-340.
23. Berner D., Cox D. P., Dahn H., J. Am. Chem. Soc., 104, 2631-2632 (1982); Abe Y., Suehiro T., Chem. Lett., 1982, 337-340.
24. Kobayashi E., Okamoto A., Asada M., Okabe M., Nagamura S., Asai A., Saito H., Gomi K., Hirata T., Cancer Res., 54, 2404-2410 (1994).
25. Asai A., Nagamura S., Saito H., J. Am. Chem. Soc., 116, 4171-4177 (1994); Asai A., Nagamura S., Saito H., Takahashi I., Nakano H., Nucleic Acids Res., 22, 83-93 (1994); Ogasawara H., Nishio K., Takeda Y., Ohmori T., Kubota N., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., Jpn. J. Cancer Res. (Gann), 85, 418-425 (1994); Okamoto A., Asai A., Saito H., Okabe M., Gomi K., ibid., 85, 1304-1311 (1994); Ogasawara H., Nishio K., Kanzawa F., Lee Y-S., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., ibid., 86, 124-129 (1995).
26. Asai A., Nagamura S., Saito H., J. Am. Chem. Soc., 116, 4171-4177 (1994); Asai A., Nagamura S., Saito H., Takahashi I., Nakano H., Nucleic Acids Res., 22, 83-93 (1994); Ogasawara H., Nishio K., Takeda Y., Ohmori T., Kubota N., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., Jpn. J. Cancer Res. (Gann), 85, 418-425 (1994); Okamoto A., Asai A., Saito H., Okabe M., Gomi K., ibid., 85, 1304-1311 (1994); Ogasawara H., Nishio K., Kanzawa F., Lee Y-S., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., ibid., 86, 124-129 (1995).
27. Asai A., Nagamura S., Saito H., J. Am. Chem. Soc., 116, 4171-4177 (1994); Asai A., Nagamura S., Saito H., Takahashi I., Nakano H., Nucleic Acids Res., 22, 83-93 (1994); Ogasawara H., Nishio K., Takeda Y., Ohmori T., Kubota N., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., Jpn. J. Cancer Res. (Gann), 85, 418-425 (1994); Okamoto A., Asai A., Saito H., Okabe M., Gomi K., ibid., 85, 1304-1311 (1994); Ogasawara H., Nishio K., Kanzawa F., Lee Y-S., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., ibid., 86, 124-129 (1995).
28. Asai A., Nagamura S., Saito H., J. Am. Chem. Soc., 116, 4171-4177 (1994); Asai A., Nagamura S., Saito H., Takahashi I., Nakano H., Nucleic Acids Res., 22, 83-93 (1994); Ogasawara H., Nishio K., Takeda Y., Ohmori T., Kubota N., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., Jpn. J. Cancer Res. (Gann), 85, 418-425 (1994); Okamoto A., Asai A., Saito H., Okabe M., Gomi K., ibid., 85, 1304-1311 (1994); Ogasawara H., Nishio K., Kanzawa F., Lee Y-S., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., ibid., 86, 124-129 (1995).
29. Asai A., Nagamura S., Saito H., J. Am. Chem. Soc., 116, 4171-4177 (1994); Asai A., Nagamura S., Saito H., Takahashi I., Nakano H., Nucleic Acids Res., 22, 83-93 (1994); Ogasawara H., Nishio K., Takeda Y., Ohmori T., Kubota N., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., Jpn. J. Cancer Res. (Gann), 85, 418-425 (1994); Okamoto A., Asai A., Saito H., Okabe M., Gomi K., ibid., 85, 1304-1311 (1994); Ogasawara H., Nishio K., Kanzawa F., Lee Y-S., Funayama Y., Ohira T., Kuraishi Y., Isogai Y., Saijo N., ibid., 86, 124-129 (1995).
30. The reduction of 3a was carried out in methanol to afford a lot of over reductive compounds. When allyl alcohol was used as a reaction solvent, the desirable hydroxy compounds at the C-3 position were predominantly obtained.
31. Details of the synthetic study of KW-2189 will be published elsewhere by M. Kinugawa et al.
32. Treatment of 4a with CSA in toluene at 50°C afforded 5a in 65% yield accompanied with 2a in 30% yield. It is probably considered that the silyl moiety of 5a was removed under acidic conditions to produce 2a during the purification process. Therefore, it is indicated that a 1, 2-shift of the methoxycarbonyl group has proceeded quantitatively.