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Stereocontrolled Crotylation of 4-Acetoxy-2-azetidinone for the Synthesis of 1β-Methylcarbapenem Precursor

  • Received : 2010.06.01
  • Accepted : 2010.07.15
  • Published : 2010.09.20
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Abstract

Keywords

References

  1. Schmitt, S. M.; Salzmann, T. N.; Shih, D. H.; Christensen, B. G. J. Antibiot. 1988, 41, 780. https://doi.org/10.7164/antibiotics.41.780
  2. Deziel, R.; Favreau, D. Tetrahedron Lett. 1989, 30, 1345. https://doi.org/10.1016/S0040-4039(00)99461-9
  3. Guthikonda, R. N.; Cama, L. D.; Quesada, M.; Woods, M. F.; Salzmann, T. N.; Christensen, B. G. J. Med. Chem. 1987, 30, 871. https://doi.org/10.1021/jm00388a022
  4. Wells, J. S.; Trejo, W. H.; Principe, P. A.; Bush, K.; Geoegopapadakou, N.; Boner, D. P.; Sykes, R. B. J. Antibiot. 1982, 35, 184. https://doi.org/10.7164/antibiotics.35.184
  5. Leanza, W. J.; Wildonger, K. J.; Miller, T. W.; Christensen, B. G. J. Med. Chem. 1979, 22, 1435. https://doi.org/10.1021/jm00198a001
  6. Yutaka, N.; Tadafumi, K.; Tetsuya, Y.; Takahiro, K. Org. Process Res. Dev. 2003, 7, 649. https://doi.org/10.1021/op0340412
  7. Kropp, H.; Sundelof, J. G.; Hajdu, R.; Kahan, F. M. Antimicrob. Agents Chemother. 1982, 22, 62. https://doi.org/10.1128/AAC.22.1.62
  8. Kobayashi, T.; Ishida, N.; Hiraoka, T. J. Chem. Soc. Chem. Comm. 1980, 736.
  9. Oida, S.; Yoshida, A.; Ohki, E. Chem. Pharm. Bull. 1980, 28, 3494. https://doi.org/10.1248/cpb.28.3494
  10. Barrett, A. G. M.; Quayle, P. J. Chem. Soc. Chem. Comm. 1981, 1076.
  11. Hirai, K.; Iwano, Y.; Fujimoto, K. Tetrahedron Lett. 1982, 23, 4025. https://doi.org/10.1016/S0040-4039(00)88686-4
  12. Deziel, R.; Favreau, D. Tetrahedron Lett. 1986, 27, 5687. https://doi.org/10.1016/S0040-4039(00)85301-0
  13. Kim, C. D.; Luh, B.; Partyka, R. A. Tetrahedron Lett. 1987, 28, 507. https://doi.org/10.1016/S0040-4039(00)95767-8
  14. Mori, M.; Oida, S. Bioorg. Med. Chem. Lett. 1993, 3, 2389. https://doi.org/10.1016/S0960-894X(01)80961-6
  15. Kondo, K.; Seki, M.; Kuroda, T.; Tamanaka, T.; Iwasaki, T. J. Org. Chem. 1997, 62, 2884.
  16. Kondo, K.; Seki, M.; Kuroda, T.; Yamanaka, T.; Iwasaki, T. J. Org. Chem. 1995, 60, 1096. https://doi.org/10.1021/jo00110a001
  17. Ito, Y.; Sasaki, A.; Tamoto, K.; Sunagawa, M.; Terashima, S. Tetrahedron 1991, 47, 2801. https://doi.org/10.1016/S0040-4020(01)87086-1
  18. Shirai, F. J.; Nakai, T. J. Org. Chem. 1987, 52, 5491. https://doi.org/10.1021/jo00233a044
  19. Fuenes, L. M.; Shinkai, I.; Salzmann, T. N. J. Am. Chem. Soc. 1986, 108, 4675. https://doi.org/10.1021/ja00275a083
  20. Shibata, T.; Sugimura, Y. J. Antibiot. 1989, 42, 374. https://doi.org/10.7164/antibiotics.42.374
  21. Shibata, T.; Iino, K.; Tanaka, T.; Hashimoto, T.; Kameyama, Y.; Sugimura, Y. Tetrahedron Lett. 1985, 26, 4739. https://doi.org/10.1016/S0040-4039(00)94938-4
  22. Uyeo, S.; Itani, H. Tetrahedron Lett. 1991, 32, 2143. https://doi.org/10.1016/S0040-4039(00)71259-7
  23. Imuta, M.; Itani, H.; Ona, H.; Hamada, Y.; Uyeo, S.; Yoshida, T. Chem. Pharm. Bull. 1991, 39(3), 663. https://doi.org/10.1248/cpb.39.663
  24. Kang, S.-K.; Baik, T.-G.; Jiao, X.-H.; Lee, K.-J.; Lee, C. H. Synlett 1999, 447.
  25. Fliri, H.; Mak, C. P. J. Org. Chem. 1985, 50, 3438. https://doi.org/10.1021/jo00219a003
  26. Katsumi, F.; Yuji, I.; Koichi, H. Tetrahedron Lett. 1985, 26, 89. https://doi.org/10.1016/S0040-4039(00)98475-2
  27. Haruta, J.; Nishi, K.; Kikuchi, K.; Matsuda, S.; Tamura, Y.; Kita, Y. Chem. Pharm. Bull. 1989, 37, 2338. https://doi.org/10.1248/cpb.37.2338
  28. Hiroshi, O.; Hiroyuki, I.; Hiroaki, O. Jpn. Kokai Tokkyo Koho 1994, JP 06340618 A 19941213.
  29. Keita, N.; Teruyoshi, K; Masafumi, F.; Yasuyoshi, U. PCT Int. Appl. 2007, WO 2007145260 Application: WO 2007-JP61937 20070613.
  30. Hikaru, I.; Shoichiro, U. Synlett 1995, 2, 213.
  31. Kim, S. H.; Kang, S. W.; Ahn, H. J.; Kim, H. R.; Kim, Y. H. Repub. Korean Kongkae Taeho Kongbo 2009, KR 2009101581 A 20090929.

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  1. ChemInform Abstract: Stereocontrolled Crotylation of 4-Acetoxy-2-azetidinone for the Synthesis of 1β-Methylcarbapenem Precursor. vol.42, pp.7, 2011, https://doi.org/10.1002/chin.201107133