Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Stereoselective Synthesis of a Novel Cyclohexene Version of Carbovir

  • Li, Hua (BK-21 Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK-21 Team, College of Pharmacy, Chosun University)
  • Published : 2007.10.20
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Abstract

This paper describes a racemic and stereoselective synthetic route for a novel cyclohexenyl carbocyclic adenine analogue. The required stereochemistry of the target compound was controlled using a stereoselective glycolate Claisen rearrangement followed by α-chelated carbonyl addition. The introduction of 6-chloropurine was achieved using Mitsunobu conditions, and further modifications of the corresponding heterocycle gave the target cyclohexenyl nucleoside.

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References

  1. Vince, R.; Hua, M.; Brownell, J.; Daluge, S.; Lee, F. C.; Shannon, W. M.; Lavelle, G. C.; Qualls, J.; Weisolw, O. S.; Kiser, R. Biochem. Biophys. Res. Commun. 1988, 156, 1046 https://doi.org/10.1016/S0006-291X(88)80950-1
  2. Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17 https://doi.org/10.1021/jm00163a004
  3. Katagiri, N.; Nomura, M.; Sato, H.; Kaneko, C.; Yusa, K.; Tsuruo, T. J. Med. Chem. 1992, 35, 1882 https://doi.org/10.1021/jm00088a026
  4. Toyoda, A.; Katagiri, N.; Kaneko, C. Heterocycles 1994, 38, 27 https://doi.org/10.3987/COM-93-6551
  5. Yarchoan, R.; Pluda, J. M.; Thomas, R. V.; Mitsuya, H.; Brouwers, P.; Wyvill, K. M.; Hartman, N.; Johns, D. G.; Broder, S. Lancet 1990, 336, 526 https://doi.org/10.1016/0140-6736(90)92085-V
  6. Huang, H.; Chopra, R.; Verdin, G. L.; Harrison, S. C. Science 1998, 282, 1669 https://doi.org/10.1126/science.282.5394.1669
  7. Rosenquist, A.; Kvarnstrom, I.; Samuelsson, B. J. Org. Chem. 1996, 61, 6282 https://doi.org/10.1021/jo9603542
  8. Wang, J.; Busson, R.; Blaton, N.; Rozenski, J.; Herdweijn, P. J. Org. Chem. 1998, 63, 3051 https://doi.org/10.1021/jo972285c
  9. Wang, J.; Herdewijn, P. J. Org. Chem. 1999, 64, 7820 https://doi.org/10.1021/jo9908288
  10. Wang, J.; Froeyen, M.; Hendrix, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 2000, 43, 736 https://doi.org/10.1021/jm991171l
  11. Wang, J.; Morral, J.; Hendrix, C.; Herdewijn, P. J. Org. Chem. 2001, 66, 8478 https://doi.org/10.1021/jo015924z
  12. Maurinsh, Y.; Schraml, I.; De Winter, H. et al. J. Org. Chem. 1997, 62, 2861 https://doi.org/10.1021/jo962204x
  13. Mikhailov, S. N.; Blaton, N.; Rosenski, J.; Balzarini, J.; De Clercq, E.; Herdewijn, P. Nucleosides Nucleotides 1996, 15, 867 https://doi.org/10.1080/07328319608002133
  14. Verheggen, I.; Van Aerschot, A.; Toppet, S.; Snoeck, R.; Janssen, G.; Balzarini, J.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 1993, 36, 2033 https://doi.org/10.1021/jm00066a013
  15. Verheggen, I.; Van Aerschot, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; Claes, P.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 1995, 38, 826 https://doi.org/10.1021/jm00005a010
  16. Vijgen, S.; Nauwelaerts, K.; Wang, J.; Van Aerschot, A.; Lagoja, I.; Herdewijn, P. J. Org. Chem. 2005, 70, 4591 https://doi.org/10.1021/jo048037f
  17. Nauwelaerts, K.; Lescrinier, E.; Sclep, G.; Herdewijn, P. Nucleic Acid Res. 2005, 33, 2452 https://doi.org/10.1093/nar/gki538
  18. Nauwelaerts, K.; Fisher, M.; Froeyen, M.; Lescrinier, E.; Van Aerschot, A.; Xu, D.; DeLong, R.; Kang, H.; Juliano, R. L.; Herdewijn, P. J. Am. Chem. Soc. 2007, 9340
  19. Wang, J.; Verbeure, B.; Luyten, I.; Froeyen, M.; Hendrix, C.; Rosemeyer, H.; Seelaa, F.; Van Aerschot, A.; Herdewijn, P. J. Am. Chem. Soc. 2000, 122, 8595 https://doi.org/10.1021/ja000018+
  20. Gu, P.; Scheoers, G.; Rozenski, J.; Van Aerschot, A.; Herdewijn, P. Oligonucleotides 2003, 13, 479 https://doi.org/10.1089/154545703322860799
  21. Hong, J. H.; Oh, C. H.; Cho, J. H. Tetrahedron 2003, 59, 6103 https://doi.org/10.1016/S0040-4020(03)00986-4
  22. Minami, N.; Ko, S. S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109 https://doi.org/10.1021/ja00368a040
  23. Hassner, A.; Alexanian, V. Tetrahedron Lett. 1978, 19, 4475 https://doi.org/10.1016/S0040-4039(01)95256-6
  24. Kazmaier, U. Liebigs Ann-Recl. 1997, 285
  25. Fujisawa, T.; Tajima, K.; Sato, T. Chem. Lett. 1984, 1669
  26. Mengel, A.; Reiser, O. Chem Rev. 1999, 99, 1191 https://doi.org/10.1021/cr980379w
  27. Reetz, M. T. Chem. Rev. 1999, 99, 1121 https://doi.org/10.1021/cr980417b
  28. Still, C. Tetrahedron Lett. 1980, 21, 1031 https://doi.org/10.1016/S0040-4039(00)78831-9
  29. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Rev. 1995, 28, 446 https://doi.org/10.1021/ar00059a002
  30. Schrock, R. R. Tetrahedron 1999, 55, 8141 https://doi.org/10.1016/S0040-4020(99)00304-X
  31. Furstner, A. Angew. Chem. Int. Ed. Engl. 2000, 39, 3013
  32. Trunka, T. M.; Grubbs, R. H. Acc. Chem. Rev. 2001, 34, 18 https://doi.org/10.1021/ar000114f
  33. Hoveya, A. H.; Schrock, R. R. Chem. Eur. J. 2001, 7, 945 https://doi.org/10.1002/1521-3765(20010302)7:5<945::AID-CHEM945>3.0.CO;2-3
  34. Kim, A.; Hong, J. H. Bull. Korean Chem. Soc. 2005, 26, 1767 https://doi.org/10.5012/bkcs.2005.26.11.1767
  35. Kim, A.; Hong, J. H. Bull. Korean Chem. Soc. 2006, 27, 976 https://doi.org/10.5012/bkcs.2006.27.7.976

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