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Recent advances in carbapenem chemistry (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Recent synthetic works of carbapenems, focused on their efficiency and applicability to synthesize a variety of substituted carbapenem derivatives for the effective screening research of the new generation carbapenem antibiotics, are reviewed.

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References

  1. J. S. Kahan, F. M. Kahan, R. Goegelman, S. A. Currie, M. Jackson, E. O. Stapley, T. W. Miller, D. Hendlin, S. Mochales, S. Hernandez, and H. B. Woodruff, The 16th Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago Abstract, N 227 (1976).

  2. H. Kropp, J. S. Kahan, F. M. Kahan, J. Sandolf, G. Darland, and J. Birnbaum, The 16th Interscience Conference on Antimicrobial Agents and Chemotherapy, Chicago, Abstract, N 228 (1976).

  3. G. A. Schonberg, B. H. Arison, O. D. Hensens, J. Hirshfield, K. Hoogsteen, E. A. Kaczka, R. E. Rhodes, J. S. Kahan, F. M. Kahan, R. W. Ratcliffe, E. Walton, L. J. Ruswinkle, R. B. Morin, and B. G. Christensen, J. Am. Chem. Soc.,100, 6491 (1978).

    Google Scholar 

  4. J. S. Kahan, F. M. Kahan, R. Goegelman, S. A. Currie, M. Jackson, E. O. Stapley, T. W. Miller, A. K. Miller, D. Hendlin, S. Mochales, S. Hernandez, H. B. Woodruff, and J. Birnbaurn, J. Antibiot.,32, 1 (1979).

    Google Scholar 

  5. J. Birnbaum, F. M. Kahan, H. Kropp, and J. S. Macdonald, Am. J. Med. (Suppl. 6A),78, 3 (1985).

    Google Scholar 

  6. T. Miyadera, Y. Sugimura, S. Oida, S. Ohya, H. Takahagi, T. Okada, M. Hisaoka, Y. Kawahara, T. Hirasawa, Sankyo Kenkyusho Nempo.,43, 1 (1991); Chem. Abstr.,117, 9664 (1992).

    Google Scholar 

  7. M. Sunagawa, H. Matsumura, T. Inoue, M. Fukasawa, and M. Kato, J. Antibiot.,43, 519 (1990).

    Google Scholar 

  8. M. Sunagawa, H. Matsumura, T. Inoue, M. Fukasawa, and M. Kato, ibid.,44, 459 (1990).

    Google Scholar 

  9. M. Sunagawa, H. Matsumura, T. Inoue, H. Yamaga, and M. Fukasawa, ibid.,45, 971 (1992).

    Google Scholar 

  10. M. Fukasawa, Y. Sumita, E. T. Harabe, T. Tanio, H. Nouda, T. Kohzuki, T. Okuda, H. Matsumura, and M. Sunagawa, Antimicrob. Agents Chemother.,36, 1577 (1957).

    Google Scholar 

  11. Y. Sumita, Y. Eguchi, M. Fukasawa, T. Okuda, H. Yamaga, H. Matsumura, and M. Sunagawa, J. Antibiot.,46, 629 (1993).

    Google Scholar 

  12. Y. Sumita, H. Yamaga, and M. Sunagawa, ibid.,48, 89 (1995).

    Google Scholar 

  13. Y. Sumita, H. Nouda, H. Shinagawa, H. Yamaga, and M. Sunagawa, ibid.,48, 188 (1995).

    Google Scholar 

  14. H. Nouda, H. Matsumura, T. Tanio, and M. Sunagawa, J. Antibiot.,49, 603 (1996)

    Google Scholar 

  15. G. B. Calandra, K. R. Brown, L. C. Grad, V. I. Ahonkhai, C. Wang, and M. A. Aziz, Am. J. Med.,78 (Suppl. 6A), 73 (1985).

    Google Scholar 

  16. Y. Ohno, A. Hirose, R. Tsuji, T. Kato, M. Nakamura, J. R. Edwards, and J. B. Patel, Chemotherapy (Tokyo),40(S-1), 175 (1992).

    Google Scholar 

  17. M. Sunagawa, H. Matsumura, and M. Fukasawa, J. Antibiot.,45, 1983 (1992).

    Google Scholar 

  18. M. Sunagawa, H. Matsumura, Y. Sumita, and H. Nouda, ibid. J. Antibiot,48, 408;

  19. M. Sunagawa and H. Nouda, Jpan. J. Antibiot.,49, 1 (1996).

    Google Scholar 

  20. D. H. Shih, F. Baker, L. Cama, and B. G. Christensen, Heterocycles,21, 29 (1994).

    Google Scholar 

  21. M. Sunagawa, H. Yamaga, H. Shinagawa, H. Houchigai, and Y. Sumita, Bioorg. Med. Chem. Lett.,4, 2793; (1994).

    Google Scholar 

  22. Y. Sumita, H. Nouda, K. Kanazawa, and M. Fukasawa, Antimicrob. Agents Chemother.,39 910 (1995).

    Google Scholar 

  23. L. C. Meurer, R. N. Guthikonda, J. L. Huber, and F. DiNinno, Bioorg. Med. Chem. Lett.,5, 767 (1995).

    Google Scholar 

  24. F. DiNinno, D. A. Muthrad, T. N. Salzmann, J. Huber, J. Kahan, and H. Kropp, ibid.,5, 945 (1995).

    Google Scholar 

  25. J. C. Arnould, R. N. Illingworth, W. W. Nichols, and R. G. Willson, ibid.,6, 2449 (1996).

    Google Scholar 

  26. H. Azami, D. Barrett, A. Tanaka, H. Sasaki, K. Matsuda, M. Sakurai, Y. Matsumoto, S. Tawara, T. Chiba, and K. Sakane, ibid.,7, 1409 (1997).

    Google Scholar 

  27. N. Ohtake, H. Imamura, H. Kiyonaga, H. Jona, M. Ogawa, S. Okada, A. Shimizu, M. Moriya, H. Sato, Y. Tominaga, K. Yamada, M. Nakano, R. Ushijima, and S. Nakagawa, ibid.,7, 1617 (1997).

    Google Scholar 

  28. H. Azami, K. Matsuda, H. Tsutsumi, T. Kamimura, and M. Murata, J. Antibiot.,51, 374 (1998).

    Google Scholar 

  29. N. Ohtake, H. Imamura, H. Jona, H. Kiyonaga, A. Shimizu, M. Moriya, H. Sato, M. Nakano, R. Ushijima, and S. Nakagawa, Bioorg. Med. Chem.,6, 1089 (1998).

    Google Scholar 

  30. S. Nakagawa, T. Hashizume, K. Matsuda, M. Sanada, O. Okamoto, H. Fukatsu, and N. Tanaka, Antimicrob. Agents Chemother.,37, 2756 (1993).

    Google Scholar 

  31. F. Ohba, M. Nakamura-Kamijo, N. Watanabe, and K. Katsu, ibid.,41, 298 (1997).

    Google Scholar 

  32. M. Tsuji, Y. Ishii, A. Ohno, S. Miyazaki, and K. Yamaguchi, ibid.,42, 94 (1998).

    Google Scholar 

  33. M. Sunagawa, A. Sasaki, H. Yamaga, H. Shinagawa, Y. Sumita and H. Nouda, J. Antibiot.,47, 1337 (1994).

    Google Scholar 

  34. J. G. Sundelof, R. Hajdu, C. J. Gill, R. Thompson H. Rosen, and H. Kropp, Antimicrob. Agents Chemother.,41, 1743 (1997).

    Google Scholar 

  35. T. Nishi, M. Takemura, T. Saito, Y. Ishida, K. Sugita, M. Houmura, H. Ishii, K. Sato, I. Hayakawa, and T. Hayano, The 32nd Interscience Conference on Antimicrobial Agents and Chemotherapy, Anaheim, Abstract, N 131 (1992).

  36. O. Okamoto, H. Fukatsu, S. Nakagawa, and N. Tanaka The 33rd Interscience Conference on Antimicrobial Agents and Chemotherapy, New Orleans, Abstract, N 898 (1993).

  37. N. Ohtake, E. Mano, R. Ushijima, M. Sanada, S. Nakagawa, and N. Tanaka, The 33rd Interscience Conference on Antimicrobial Agents and Chemotherapy, New Orleans, Abstract, N 921 (1993).

  38. S. Sasaki, K. Murakami, Y. Nishitani, and S. Kuwahara, The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Orlando, Abstract, N F33 (1994).

  39. N. Sato, M. Sasho, A. Kamada, T. Suzuki, K. Ashizawa, and I. Sugiyama, The 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, Abstract, N F151 (1995).

  40. H. Azami, D. Barrett, A. Tanaka, H. Sasaki, K. Matsuda, T. Chiba, Y. Matsumoto, S. Matsumoto, C. Morinaga, K. Ishiguro, S. Tawara, K. Sakane, and H. Takasugi, Bioorg. Med. Chem. Lett.,5, 2199 (1995).

    Google Scholar 

  41. B. A. Pelak, L. S. Gerckens, P. M. Scott, C. Gill, L. Pacholok, L. Lynch, K. Dorso, J. Kohler, D. Shungu, and H. Kropp, The 36th Interscience Conference on Antimicrobial Agents and Chemotherapy, New Orleans, Abstract, N F119 (1996).

  42. H.-W. Lee, E.-N. Kim, H.-J. Son, S.-K. Ahn, K.-H. Chung, J.-W. Kim, and C.-R. Lee, Chem. Pharm. Bull.,44, 2326 (1996).

    Google Scholar 

  43. H. Azami, D. Barrett, T. Chiba, A. Fujikawa, K. Sakane, and F. Shirai,-ibid.,45, 209 (1997).

    Google Scholar 

  44. H. Azami, H. Tsutsumi, K. Matsuda, D. Barrett, K. Hattori, T. Nakajima, S. Kuroda, T. Kamimura, and M. Murata, Bioorg. Med. Chem.,5, 2069 (1997).

    Google Scholar 

  45. H.-W. Lee, E.-N. Kim, T.-W. Kang, S.-K. Ahn, N.-H. Choi, J.-W. Kim, and C. I. Hong, J. Antibiot.,50, 1078 (1997).

    Google Scholar 

  46. S. H. Kim, H. J. Shim, W. B. Kim, and M. G. Lee, Antimicrob. Agents Chemother.,42, 1217 (1998).

    Google Scholar 

  47. G. Schmidt, W. Schrock, and R. Endermann, Bioorg. Med. Chem. Lett.,3, 2193 (1993).

    Google Scholar 

  48. T. Wollmann, U. Gerlach, R. Horlein, N. Krass, R. Lattrell, M. Limbert, and A. Markus, Spec. Publ., R. Soc. Chem. (Recent Advances in the Chemistry of Anti-Infective Agents),119, 50 (1993).

    Google Scholar 

  49. A. Padova, S. M. Roberts, D. Donati, A. Perboni, and T. Rossi, J. Chem. Soc. Chem. Commun., 441 (1994).

  50. R. D. Fabio, A. Feriani, G. Gaviraghi, and T. Rossi, Bioorg. Med. Chem. Lett.,5, 1235 (1995).

    Google Scholar 

  51. C. Bismara, R. D. Fabio, D. Donati, T. Rossi, and R. J. Thomas, Tetrahedron Lett.,36, 4283 (1995).

    Google Scholar 

  52. S. Hanessian, M. J. Rozema, G. B. Reddy, and J. F. Braganza, Bioorg. Med. Chem. Lett.,5, 2535 (1995).

    Google Scholar 

  53. D. Andreotti, T. Rossi, G. Gaviraghi, D. Donati, C. Marchioro, E. D. Modugno, and A. Perboni, ibid.6, 491 (1996).

    Google Scholar 

  54. S. Biondi, G. Gaviraghi, and T. Rossi, ibid.,6, 525 (1996).

    Google Scholar 

  55. R. Camerini, M. Panunzio, G. Bonanomi, D. Donati, and A. Perboni, Tetrahedron Lett.,37, 2467 (1996).

    Google Scholar 

  56. C. Ghiron, E. Piga, T. Rossi, B. Tamburuni, and R. J. Thomas, ibid.,37, 3891 (1996).

    Google Scholar 

  57. P. M. Jackson, S. M. Roberts, S. Davalli, D. Donati, C. Marchioro, A. Perboni, and T. Rossi, J. Chem. Soc., Perkin Trans. I, 2029 (1996).

    Google Scholar 

  58. M. E. Tranguiillini, G. L. Araldi, D. Donati, G. Pentassuglia, A. Pezzoli, and A. Ursini, Bioorg. Med. Chem. Lett.,6, 1683 (1996).

    Google Scholar 

  59. M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron: Asymmetry,7, 2929 (1996).

    Google Scholar 

  60. S. Hanessian and M. J. Rozema, J. Am. Chem. Soc.,118, 9884 (1996).

    Google Scholar 

  61. S. Hanessian, A. M. Griffin, and M. J. Rozema, Bioorg. Med. Chem. Lett.,7, 1857 (1997).

    Google Scholar 

  62. S. M. Sakya, T. W. Strohmeyer, S. A. Lang, and Y.-I. Lin, Tetrahedron Lett.,38, 5913 (1997).

    Google Scholar 

  63. S. Biondi, E. Piga, T. Rossi, and G. Vigelli, ibid.,7, 2061 (1997).

    Google Scholar 

  64. T. Kametani, K. Fukumoto, and M. Ihara, Heterocycles,17, 463 (1982).

    Google Scholar 

  65. Chemistry and Biology of β-Lactam Antibiotics, Vol. 2, R. B. Morin and M. Gorman (eds.), Academic Press, Inc., New York (1982), p. 227.

    Google Scholar 

  66. W. Durckheimer, J. Blumbach, R. Lattrell, and K. H. Scheunemann, Angew. Chem. Int. Ed. Engl.,24, 180 (1985).

    Google Scholar 

  67. T. Nagahara and T. Kametani, Heterocycles,25, 729 (1987).

    Google Scholar 

  68. Recent Progress in the Chemical Synthesis of Antibiotics, G. Lukacs and M. Ohno (eds.), Springer-Verlag, Berlin (1990), p. 565.

    Google Scholar 

  69. A. H. Berks, Tetrahedron,52, 331 (1990), and references therein.

    Google Scholar 

  70. R. W. Ratcliffe, T. N. Salzmann, and B. G. Christensen, Tetrahedron Lett.,21, 31 (1980).

    Google Scholar 

  71. L. D. Cama and B. G. Christensen, J. Am. Chem. Soc.,100, 8006 (1978).

    Google Scholar 

  72. A. J. G. Baxter, P. Davis, R. J. Ponsford, and R. Southgate, Tetrahedron Lett.,21, 5071 (1980).

    Google Scholar 

  73. A. Yoshida, Y. Tajima, N. Takeda, and S. Oida, ibid.,25, 2793 (1984).

    Google Scholar 

  74. M. Hatanaka, Y. Yamamoto, H. Nitta, and T. Ishimaru, Tetrahedron Lett.,22, 3883 (1981).

    Google Scholar 

  75. T. Shibata, K. Iino, T. Tanaka, T. Hashimoto, Y. Kameyama, and Y. Sugimura, Tetrahedron Lett.,26, 4739 (1985).

    Google Scholar 

  76. R. N. Guthikonda, L. D. Cama, M. Quesada, M. F. Woods, T. N. Salzmann, and B. G. Christensen, J. Med. Chem.,30, 871 (1987).

    Google Scholar 

  77. S. M. Schmitt, T. N. Salzmann, D. H. Shih, and B. G. Christensen, J. Antibiot.,41, 780 (1988).

    Google Scholar 

  78. T. J. Sowin and A. I. Meyers, J. Org. Chem.,53, 4156 (1988).

    Google Scholar 

  79. R. Deziel and D. Favreau, Tetrahedron Lett.,30, 1345 (1989).

    Google Scholar 

  80. T. Shibata and Y. Sugimura, J. Antibiot.,42, 374 (1989).

    Google Scholar 

  81. T. N. Salzmann, F. P. DiNinno, M. L. Greenlee, R. N. Guthikonda, M. L. Quesada, S. M. Schmitt, J. J. Herrmann, and M. F. Woods, Recent Advances in the Chemistry of β-Lactam Antibiotics, P. H. Bentley and R. Southgate (eds.), The Royal Society of Chemistrv, London (1989), p. 171.

    Google Scholar 

  82. M. Sunagawa, A. Sasaki, H. Matsumura, K. Goda, and K. Tamoto, Chem. Pharm. Bull.,42, 1381 (1994).

    Google Scholar 

  83. M. A. Williams and M. J. Miller, Tetrahedron Lett.,31, 1807 (1990).

    Google Scholar 

  84. M. A. Williams, C.-N. Hsiao, and M. J. Miller, J. Org. Chem.,56, 2688 (1991).

    Google Scholar 

  85. M. Kume, T. Kubota, and Y. Iso, Tetrahedron Lett.,36, 8043 (1995).

    Google Scholar 

  86. G. B. Feigelson, ibid.,34, 4747 (1993).

    Google Scholar 

  87. G. B. Feigelson, ibid.,36, 7407 (1995).

    Google Scholar 

  88. O. Sakurai, M. Takahashi, T. Ogiku, M. Hayashi, H. Horikawa, and T. Iwasaki, ibid.,35, 6317 (1994).

    Google Scholar 

  89. O. Sakurai, T. Ogiku, M. Takahashi, H. Horikawa, and T. Iwasaki, Tetrahedron Lett.,35, 2187 (1994).

    Google Scholar 

  90. O. Sakurai, T. Ogiku, M. Takahashi, M. Takahashi, M. Hayashi, T. Yamanaka, H. Horikawa, and T. Iwasaki, J. Org. Chem.,61, 7889 (1996).

    Google Scholar 

  91. M. Seki, K. Kondo, and T. Iwasaki, Synlett., 315 (1995).

  92. K. Kondo, M. Seki, T. Kuroda, T. Yamanaka and T. Iwasaki, J. Org. Chem.,62, 2877 (1997).

    Google Scholar 

  93. O. Sakurai and H. Horikawa, Tetrahedron Lett.37, 7811 (1996).

    Google Scholar 

  94. S. Hanessian, D. Desilets, and Y. L. Bennani, ibid.,55, 3098 (1990).

    Google Scholar 

  95. S. Roland, J. O. Durand, M. Savignac, J. P. Genet, and F. Jung, Tetrahedron Lett.,36, 3007 (1995).

    Google Scholar 

  96. J. Anaya, D. H. R. Barton, S. D. Gero, M. Grande, N. Martin, and C. Tachdijian, Angew. Chem. Int. Ed. Engl.32, 867 (1993).

    Google Scholar 

  97. O. Sakurai, H. Horikawa, and T. Iwasaki, J. Chem. Soc., Chem. Commun., 2527 (1995).

  98. S. R. Martel, R. Wisedale, T. Gallagher, L. D. Hall, M. F. Mahon, R. H. Bradbury, and N. J. Hales, J. Am. Chem. Soc.,119, 2309 (1997).

    Google Scholar 

  99. S. H. Kang and H. S. Lee, Tetrahedron Lett.,36, 6713 (1995).

    Google Scholar 

  100. M. E. Jung and B. T. Vu, J. Org. Chem.,61, 4427 (1996).

    Google Scholar 

  101. H. Ishibashi, C. Kameoka, K. Kodama, and M. Ikeda, Synlett. 915 (1995).

  102. H. Ishibashi, C. Kameoka, K. Kodama, H. Kawanami, M. Hamada, and M. Ikeda, Tetrahedron,53, 9611 (1977).

    Google Scholar 

  103. M. Nishiuchi, K. Honda, and T. Nakai, Chem. Lett., 321 (1996).

  104. A. V. Rao, M. K. Gurjar, and B. Ashok, Tetrahedron: Asymmetry,2, 255 (1991).

    Google Scholar 

  105. D. Tanner, Pure and Appl. Chem.,65, 1319 (1993).

    Google Scholar 

  106. T. Fujisawa, R. Hayakawa, and M. Shimizu, Chem. Lett., 1013 (1995).

  107. D. R. Bender, A. M. DeMarco, D. G. Melillo, S. M. Riseman, and I. Shinkai, J. Org. Chem.,57, 2411 (1992).

    Google Scholar 

  108. Y. Ueda and V. Vinet, J. Antibiot.45, 940 (1992).

    Google Scholar 

  109. Y. Sendo, M. Kii, M. Sakanoue, K. Motokawa, and Y. Kimura, Chem. Pharm. Bull.,40, 2410 (1992).

    Google Scholar 

  110. P. Remuzon, D. Bouzard, P. DiCesare, M. Essiz, J.-P. Jacquet, A. Nicolau, A. Martel, M. Menard, and C. Bachand, Tetrahedron,51, 9657 (1995).

    Google Scholar 

  111. Y. Nagao, T. Abe, H. Shimizu, T. Kumagai, and Y. Inoue, J. Chem. Soc. Chem. Commun., 821 (1989).

  112. N. V. Shah and L. D. Cama, Heterocycles,25, 221 (1987).

    Google Scholar 

  113. K. J. Wildonger, W. J. Leanza, R. W. Ratcliffe, and J. P. Springer ibid.,41, 1891 (1985).

    Google Scholar 

  114. M. Ihara, K. Satoh, Y. Ishida, N. Taniguchi, Y. Tokunaga, M. Takemura, and K. Fukumoto, ibid.,42, 437 (1996).

    Google Scholar 

  115. H. Mastalerz and M. Menard, J. Org. Chem.59, 3223 (1994).

    Google Scholar 

  116. G. Bouthillier, H. Mastalerz, and M. Menard, Tetrahedron Lett.,35, 4689 (1994).

    Google Scholar 

  117. J. H. Bateson, A. M. Robins, and R. Southgate, J. Chem. Soc. Perkin Trans.I, 2399 (1991).

    Google Scholar 

  118. R. L. Rosati, L. V. Kapili, P. Morrissey, and J. A. Retsema, J. Med. Chem.,33, 291 (1990).

    Google Scholar 

  119. K. Oda and A. Yoshida, Tetrahedron Lett.,38, 5687 (1997).

    Google Scholar 

  120. T. A. Rano, M. L. Greenlee, and F. P. DiNinno, Tetrahedron Lett.,31, 2853 (1990).

    Google Scholar 

  121. N. Yasuda, L. Xavier, D. L. Li, Y. Rieger, A. E. DeCamp, and U.-H. Dolling, ibid.,34, 3211 (1993).

    Google Scholar 

  122. Y. Narukawa, K. Nishi, and H. Onoue, ibid.,37, 2589 (1996).

    Google Scholar 

  123. Y. Narukawa, K. Nishi, and H. Onoue, Tetrahedron,53, 539 (1997).

    Google Scholar 

  124. K. Nishi, Y. Narukawa, and H. Onoue, Tetrahedron Lett.,37, 2987 (1996).

    Google Scholar 

  125. K. D. Dykstra and F. DiNinno, ibid.,39, 1865 (1998).

    Google Scholar 

  126. J. C. Arnould, F. Landier, and M. J. Pasquet, Tetrahedron Lett.,33, 7133 (1992).

    Google Scholar 

  127. M. Imuta, H. Itani, H. Ona, Y. Hamada, S. Uyeo, and T. Yoshida, Chem. Pharm. Bull.,39, 663 (1991).

    Google Scholar 

  128. S. Uyeo and H. Itani, Tetrahedron Lett.,35, 4377 (1994).

    Google Scholar 

  129. X. E. Hu and T. P. Demuth, Jr., J. Org. Chem.63, 1719 (1998).

    Google Scholar 

  130. C. Yang and N. Yasuda, Bioorg. Med. Chem. Lett.,8, 255 (1998).

    Google Scholar 

  131. Y. Nagao, T. Abe, H. Shimizu, T. Kumagai, and Y. Inoue, Heterocycles33, 523 (1992).

    Google Scholar 

  132. S. Coulto and I. Francois, J. Chem. Soc. Perkin Trans.I, 2699, (1991).

    Google Scholar 

  133. G. Bouthillier, H. Mastalerz, and M. Menard, Tetrahedron Lett.,32, 1032 (1991).

    Google Scholar 

  134. H. Mastalerz and M. Menard, Heterocycles,32, 93 (1991).

    Google Scholar 

  135. E. H. Ruediger and C. Solomon, J. Org. Chem.,56, 3183 (1991).

    Google Scholar 

  136. G. Bouthillier, H. Mastalerz, M. Menard, J. Fung-Tomc, and E. Gradelski, J. Antibiot.,45, 240 (1992).

    Google Scholar 

  137. H. Mastalerz, M. Menard, E. Ruediger, and J. Fung-Tomc, J. Med. Chem.,35, 953 (1992).

    Google Scholar 

  138. V. S. Rao, R. Remillard, and M. Menard, Heteroat. Chem.,3, 25 (1992).

    Google Scholar 

  139. M. Menard, J. Banville, A. Martel, J. Desiderio, J. Fung-Tomc, and R. A. Partyka, Spec. Publ. R. Soc. Chem. (Recent Advances in the Chemistry of Anti-Infective Agents),119, 3 (1993).

    Google Scholar 

  140. J. H. Bateson, A. M. Robins, and R. Southgate, J. Chem. Soc., Perkin Trans.I, 29 (1991).

    Google Scholar 

  141. J. V. Heck and B. G. Christensen, Tetrahedron Lett.,22, 5027 (1981).

    Google Scholar 

  142. S. Uyeo and H. Itani, Tetrahedron Lett.,32, 2143 (1991).

    Google Scholar 

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  1. Akira Sasaki
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  2. Makoto Sunagawa
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Additional information

Part of this review was published in Japanese [Yuki Gosei Kagaku Kyokaishi, 54, 761 (1996); Chem. Abstr., 125, 221386 (1996)].

Sumitomo Pharmaceuticals Research Center 1–98, Kasugadenaka 3-chome, Konohana-ku, Osaka 554, Japan. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1475–1493, November, 1998.

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Sasaki, A., Sunagawa, M. Recent advances in carbapenem chemistry (review). Chem Heterocycl Compd 34, 1249–1265 (1998). https://doi.org/10.1007/BF02256805

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