Synthetic application of chiral 4-methoxy-2-oxazolidinone synthons to 2-amino alcohols of biological interest

Heterocycles

Volumn 42, Issue 2, 1996, Pages 837-848

  Ishizuka, Tadao ^a   Morooka, Kohei ^a   Ishibuchi, Seigo ^a   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001003796     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s93     Document Type: Article

References (34)

1. H.Umezawa, T. Aoyagi, H. Morishima, M. Matsuzaki, M. Hamada, and T. Takeuchi, J. Antibiot., 1970, 23, 259 ; T. Aoyagi, H. Tobe, F. Kojima, M. Hamada, T. Takeuchi, and H. Umezawa, ibid., 1978, 31, 636 ; H. Umezawa, T. Aoyagi, H. Suda, M. Hamada, and T. Takeuchi, J. Antibiot., 1976, 29, 97.
2. H.Umezawa, T. Aoyagi, H. Morishima, M. Matsuzaki, M. Hamada, and T. Takeuchi, J. Antibiot., 1970, 23, 259 ; T. Aoyagi, H. Tobe, F. Kojima, M. Hamada, T. Takeuchi, and H. Umezawa, ibid., 1978, 31, 636 ; H. Umezawa, T. Aoyagi, H. Suda, M. Hamada, and T. Takeuchi, J. Antibiot., 1976, 29, 97.
3. H.Umezawa, T. Aoyagi, H. Morishima, M. Matsuzaki, M. Hamada, and T. Takeuchi, J. Antibiot., 1970, 23, 259 ; T. Aoyagi, H. Tobe, F. Kojima, M. Hamada, T. Takeuchi, and H. Umezawa, ibid., 1978, 31, 636 ; H. Umezawa, T. Aoyagi, H. Suda, M. Hamada, and T. Takeuchi, J. Antibiot., 1976, 29, 97.
4. A. Grein, C. Spella, A. DiMarco, and G. Canevazzi, Giorn. Microbiol., 1967, 11, 109 ; A. DiMarco, P. Gaetani, P. Orezzi, B. Scarpinato, R. Silverstrini, M. Soldati, T. Dasdia, and L. Valentini, Nature, 1964, 201, 706 ; F. Arcamone, G. Cassinelli, P. Orezzi, G. Franceschi, and R. Mondelli, J. Amer. Chem. Soc., 1964, 86, 5334 ; R. H. Iwamoto, P.Lim, and N.S.Bhacca, Tetrahedron Lett., 1968, 3891.
5. A. Grein, C. Spella, A. DiMarco, and G. Canevazzi, Giorn. Microbiol., 1967, 11, 109 ; A. DiMarco, P. Gaetani, P. Orezzi, B. Scarpinato, R. Silverstrini, M. Soldati, T. Dasdia, and L. Valentini, Nature, 1964, 201, 706 ; F. Arcamone, G. Cassinelli, P. Orezzi, G. Franceschi, and R. Mondelli, J. Amer. Chem. Soc., 1964, 86, 5334 ; R. H. Iwamoto, P.Lim, and N.S.Bhacca, Tetrahedron Lett., 1968, 3891.
6. A. Grein, C. Spella, A. DiMarco, and G. Canevazzi, Giorn. Microbiol., 1967, 11, 109 ; A. DiMarco, P. Gaetani, P. Orezzi, B. Scarpinato, R. Silverstrini, M. Soldati, T. Dasdia, and L. Valentini, Nature, 1964, 201, 706 ; F. Arcamone, G. Cassinelli, P. Orezzi, G. Franceschi, and R. Mondelli, J. Amer. Chem. Soc., 1964, 86, 5334 ; R. H. Iwamoto, P.Lim, and N.S.Bhacca, Tetrahedron Lett., 1968, 3891.
7. A. Grein, C. Spella, A. DiMarco, and G. Canevazzi, Giorn. Microbiol., 1967, 11, 109 ; A. DiMarco, P. Gaetani, P. Orezzi, B. Scarpinato, R. Silverstrini, M. Soldati, T. Dasdia, and L. Valentini, Nature, 1964, 201, 706 ; F. Arcamone, G. Cassinelli, P. Orezzi, G. Franceschi, and R. Mondelli, J. Amer. Chem. Soc., 1964, 86, 5334 ; R. H. Iwamoto, P.Lim, and N.S.Bhacca, Tetrahedron Lett., 1968, 3891.
8. T. Ishizuka and T. Kunieda, J. Syn. Org. Chem. Jpn. 1991, 49, 1841 ; T. Ishizuka, S. Ishibuchi, and T. Kunieda, Tetrahedron, 1993, 49, 1841 ; T. Kunieda and T. Ishizuka, 'Studies in natural Products Chemistry (Part H).' vol. 12, ed. by Atta-ur Rahmann Elsevier Science Publishers, Amsterdam, 1993, pp. 411-444 ; T. Ishizuka and T. Kunieda, Yakugaku Zasshi, 1995, 115, 460.
9. T. Ishizuka and T. Kunieda, J. Syn. Org. Chem. Jpn. 1991, 49, 1841 ; T. Ishizuka, S. Ishibuchi, and T. Kunieda, Tetrahedron, 1993, 49, 1841 ; T. Kunieda and T. Ishizuka, 'Studies in natural Products Chemistry (Part H).' vol. 12, ed. by Atta-ur Rahmann Elsevier Science Publishers, Amsterdam, 1993, pp. 411-444 ; T. Ishizuka and T. Kunieda, Yakugaku Zasshi, 1995, 115, 460.
10. T. Ishizuka and T. Kunieda, J. Syn. Org. Chem. Jpn. 1991, 49, 1841 ; T. Ishizuka, S. Ishibuchi, and T. Kunieda, Tetrahedron, 1993, 49, 1841 ; T. Kunieda and T. Ishizuka, 'Studies in natural Products Chemistry (Part H).' vol. 12, ed. by Atta-ur Rahmann Elsevier Science Publishers, Amsterdam, 1993, pp. 411-444 ; T. Ishizuka and T. Kunieda, Yakugaku Zasshi, 1995, 115, 460.
11. T. Ishizuka and T. Kunieda, J. Syn. Org. Chem. Jpn. 1991, 49, 1841 ; T. Ishizuka, S. Ishibuchi, and T. Kunieda, Tetrahedron, 1993, 49, 1841 ; T. Kunieda and T. Ishizuka, 'Studies in natural Products Chemistry (Part H).' vol. 12, ed. by Atta-ur Rahmann Elsevier Science Publishers, Amsterdam, 1993, pp. 411-444 ; T. Ishizuka and T. Kunieda, Yakugaku Zasshi, 1995, 115, 460.
12. T. Ishizuka, S. Ishibuchi, and T. Kunieda, Tetrahedron Lett., 1989, 30, 3449.
13. S. Ishibuchi, T. Nagatani, T. Ishizuka, and T. Kunieda, Natural Product Lett., 1992, 1, 21.
14. For a review : R. W. Miller, J. Nat. Prod., 1980, 43, 425.
15. M-C. Bissery, D.Guénard, F.Guéritte-Voegelein, and F. Lavelle, Cancer Res., 1991, 51, 4845 ; F.Guéritte-Voegelein, D.Guénard, F. Lavelle, M-T. LeGoff, L. Magatal, and P. Potier, J. Med. Chem., 1991, 34, 992 ; A. Correa, J-N. Denis, M-J.Luche, and A. E. Green, J. Org. Chem., 1993, 58, 255.
16. M-C. Bissery, D.Guénard, F.Guéritte-Voegelein, and F. Lavelle, Cancer Res., 1991, 51, 4845 ; F.Guéritte-Voegelein, D.Guénard, F. Lavelle, M-T. LeGoff, L. Magatal, and P. Potier, J. Med. Chem., 1991, 34, 992 ; A. Correa, J-N. Denis, M-J.Luche, and A. E. Green, J. Org. Chem., 1993, 58, 255.
17. M-C. Bissery, D.Guénard, F.Guéritte-Voegelein, and F. Lavelle, Cancer Res., 1991, 51, 4845 ; F.Guéritte-Voegelein, D.Guénard, F. Lavelle, M-T. LeGoff, L. Magatal, and P. Potier, J. Med. Chem., 1991, 34, 992 ; A. Correa, J-N. Denis, M-J.Luche, and A. E. Green, J. Org. Chem., 1993, 58, 255.
18. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
19. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
20. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
21. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
22. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
23. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
24. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
25. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
26. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
27. M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans. 1, 1994, 2385 ; K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785 ; J-N. Denis, A. M. Kanazawa, and A. E. Green, Tetrahedron Lett., 1994, 35, 105 ; R. N. Patel, A. Banerjee, J. M. Howell, C. G. McNamee, D. Brozozowski, D. Mirfakhrae, V. Nanduri, J. K. Thottathil, and L. J. Szarka, Tetrahedron : Asymmetry, 1993, 4, 2069 ; M. E. Bunnage, S. G. Davies, and C. J. Goodwin, J. Chem. Soc., Perkin Trans, 1, 1993, 1375 ; A. E. Kanazawa, A. Correa, J-N. Danis, M. J. Marie, and A. E. Green, J. Org. Chem., 1993, 58, 255 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1991, 56, 6939 ; I. Ojima, I. Habus, and M. Zhao, J. Org. Chem., 1991, 56, 1681 ; J-N. Denis, A. Correa, and A. E. Greene, J. Org. Chem., 1990, 55, 1957 ; J-N. Denis, A. E. Greene, A. A. Serra, and M-J. Luche, J. Org. Chem., 1986, 51, 46.
28. S. Ishibuchi, Y. Ikematsu, T. Ishizuka, and T. Kunieda, Tetrahedron Lett., 1991, 32, 3523.
29. A. Commerçon, D. Bézard, F. Bernard, and J. D. Bourzat, Tetrahedron Lett., 1992, 33, 5185.
30. N. K. Gulavita and P.J. Scheuer, J. Org. Chem., 1989, 54, 366.
31. K. Mori and H. Matsuda, Liebigs Ann. Chem., 1992, 131.
32. K.-A. Karlsson, 'Biological Membranes,' ed. by D. Chapman, Academic Press, London, 1982, 4, 1.
33. Isolation : J. Kobayashi, M. Ishibashi, H. Nakamura, Y. Hirata, T. Yamasu, T. Sasaki, and Y. Ohizumi, Experientia, 1988, 44, 800 ; synthesis : Y. Yoshida, M. Nakagawa, H. Seki, and T. Hino, J. Chem. Soc., Perkin Trans. 1, 1992, 343.
34. Isolation : J. Kobayashi, M. Ishibashi, H. Nakamura, Y. Hirata, T. Yamasu, T. Sasaki, and Y. Ohizumi, Experientia, 1988, 44, 800 ; synthesis : Y. Yoshida, M. Nakagawa, H. Seki, and T. Hino, J. Chem. Soc., Perkin Trans. 1, 1992, 343.