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Synthesis of 4'α-C Phenyl-Branched Carbocyclic Nucleoside Using Ring-Closing Metathesis

  • Published : 2003.09.20

Abstract

An efficient synthetic route for preparing novel $4'{\alpha}$-C phenyl branched carbocyclic nucleoside is described. The installation of phenyl group at the $4'$-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) beginning from simple ketone such as 2-hydroxy acetophenone.

Keywords

References

  1. Stoeckler, J. D.; Cambor, C.; Parks, R. E., Jr. Biochemistry 1980, 19, 102. https://doi.org/10.1021/bi00542a016
  2. Daluge, S. M.; Good, S. S.; Faletto, M. B.; Miller, W. H.; StClair, M. H.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J.E.; Dornsife, R. E.; Averett, D. R.; Krenitsky, T. A. Antimicrob.Agents Chemother. 1997, 41, 1082
  3. Dobkin, J. F. Infect. Med.1999, 17, 625.
  4. Maag, H.; Rydzewski, R. M.; McRoberts, M. J.; Verheyden, J.P. H.; Prisbe, E. J. J. Med. Chem. 1992, 35, 1440 https://doi.org/10.1021/jm00086a013
  5. Chen, M. S.;Suttmann, R. T.; Papp, E.; Cannon, P. D.; McRobert, M. J.; Bach,C.; Copeland, W. C.; Wang, T. S. F. Biochemistry 1993, 32, 6002 https://doi.org/10.1021/bi00074a011
  6. Maag, H.; Nelson, J. T.; Rios-Steiner, J. L.; Prisbe, E. J. J.Med. Chem. 1994, 37, 431 https://doi.org/10.1021/jm00030a001
  7. Maguire, A. R.; Meng, W. G.;Roberts, S. M.; Willetts, A. J. J. Chem. Soc., Perkin Trans. 1 1993,1795
  8. Jenkins, I. D.; Verheyden, J. P. H.; Moffatt, J. G. J. Am.Chem. Soc. 1976, 98, 3346 https://doi.org/10.1021/ja00427a049
  9. Guillerm, D.; Muzard, M.; Allart,B.; Guillerm, G. Bioorg. Med. Chem. Lett. 1995, 5, 1455 https://doi.org/10.1016/0960-894X(95)00256-S
  10. Crich, D.; Hao, X. J. Org. Chem. 1999, 64, 4016 https://doi.org/10.1021/jo990046e
  11. Crich, D.;Hao, X. J. Org. Chem. 1998, 63, 3796 https://doi.org/10.1021/jo980301f
  12. Jung, M. E.; Toyota, A.J. Org. Chem. 2001, 66, 2624 https://doi.org/10.1021/jo001223a
  13. Brown, B.; Hegedus, L .S. J.Org. Chem. 2000, 65, 1865 https://doi.org/10.1021/jo9919759
  14. Hegedus, L. S.; Geisler, L.;Riches, A. G.; Salman, S. S.; Umbricht, G. J. Org. Chem. 2002,67, 7649 https://doi.org/10.1021/jo020151f
  15. Hegedus, L. S.; Hervert, K. L.; Matsui, S. J. Org.Chem. 2002, 67, 4076. https://doi.org/10.1021/jo011074b
  16. Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matuda, A. Bioorg.Med. Chem. Lett. 1999, 9, 385. https://doi.org/10.1016/S0960-894X(99)00010-4
  17. Nomura, M.; Shuto, S.; Tanaka, M.; Sasaki, T.; Mori, S.;Shigeta, S.; Matsuda, A. J. Med. Chem. 1999, 42, 2901 https://doi.org/10.1021/jm990050i
  18. Ohrui,H.; Kohgo, S.; Kitano, K.; Sakata, S.; Kodama, E.; Yoshimura, K.;Matsuoka, M.; Shigeta, S.; Mitsuya, H. J. Med. Chem. 2000, 43,4516. https://doi.org/10.1021/jm000209n
  19. O'Yang, C.; Wu, H. Y.; Fraser-Smith, E. B.; Walker, K. A. M.Tetrahedron Lett. 1992, 33, 37. https://doi.org/10.1016/S0040-4039(00)77667-2
  20. Ko, O. H.; Hong, J. H.Tetrahedron Lett. 2002, 43, 6399 https://doi.org/10.1016/S0040-4039(02)01384-9
  21. Hong, J. H.; Gao, M. Y.;Choi, Y.; Cheng, Y.-C.; Schinazi, R. F.; Chu, C. K. CarbohydrateRes. 2000, 328, 37 https://doi.org/10.1016/S0008-6215(00)00005-7
  22. Hong, J. H.; Gao, M. Y.; Chu, C. K.Tetrahedron Lett. 1999, 40, 231 https://doi.org/10.1016/S0040-4039(98)02324-7
  23. Hong, J. H.; Lee, K.; Choi, Y.;Chu, C. K. Tetrahedron Lett. 1988, 39, 3443. https://doi.org/10.1016/S0040-4039(98)00567-X
  24. Hong, J. H.; Shim, M.J.; Ro, B. O.; Ko, O. H. J. Org. Chem. 2002, 67, 6387 https://doi.org/10.1021/jo025984k
  25. Ewing,D.; Glacon, V.; Mackenzie, G.; Postel, D.; Len, C. TetrahedronLett. 2002, 43, 3503 https://doi.org/10.1016/S0040-4039(02)00572-5
  26. Gurjar, M. K.; Maheshwar, K. J. Org.Chem. 2001, 66, 7552 https://doi.org/10.1021/jo010718c
  27. Crimmins, M. T.; King, B. W.;Zuercher, W. J.; Choy, A. L. J. Org. Chem. 2000, 65, 8499. https://doi.org/10.1021/jo005535p
  28. Trost, B. M.;Kallander, L. S. J. Org. Chem. 1999, 64, 5427 https://doi.org/10.1021/jo990195x
  29. Trost, B. M.;Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037 https://doi.org/10.1021/ja9537336
  30. Deardorff, D. R.;Savin, K. A.; Justman, C. J.; Karanjawala, Z. E.; Sheppeck,II, J. E.; Hager, D. C.; Aydin, N. J. Org. Chem. 1996, 61, 3616 https://doi.org/10.1021/jo951510s
  31. Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S.Chemistry Lett. 1994, 1071
  32. Evans, C. T.; Roberts, S. M.;Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc. Perkin Trans 11992, 589.
  33. Waga, T.; Ohriu, H.; Meguro, H. Nucleosides & Nucleotides1996, 15, 287 https://doi.org/10.1080/07328319608002385
  34. Waga, T.; Nishizaki, T.; Miyakawa, J.;Ohriu, H.; Meguro, H. Biosci. Biotechnol. Biochem. 1993, 57,1433. https://doi.org/10.1271/bbb.57.1433
  35. Kato, K.; Suzuki, H.; Tanaka, H.; Miyasaka, T.; Baba, M.;Yamaguchi, K.; Akita, H. Chem. Pharm. Bull. 1999, 47, 1256. https://doi.org/10.1248/cpb.47.1256
  36. Haines, D. R.; Tseng, C. K. H.; Marquez, V. E. J. Med. Chem.1987, 30, 943 https://doi.org/10.1021/jm00388a036
  37. Jeong, L. S.; Lee, Y. A.; Moon, H. R.; Chun, M.W. Nucleosides & Nucleotides 1998, 17, 1473. https://doi.org/10.1080/07328319808003481
  38. Hossain, N.; Rozenski, J.; De Clercq, E.; Herdewjn, P.Tetrahedron 1996, 52, 13655 https://doi.org/10.1016/0040-4020(96)00818-6
  39. Jeon, G. S.; Nair, V. Tetrahedron1996, 52, 12643. https://doi.org/10.1016/0040-4020(96)00766-1
  40. Gundersen, L.-L.; Benneche, T.; Undheim, K. TetrahedronLett. 1992, 33, 1085 https://doi.org/10.1016/S0040-4039(00)91867-7
  41. Gundersen, L.-L.; Benneche, T.; Rise, F.;Gogoll, A.; Undheim, K. Acta Chem. Scand. 1992, 46, 761. https://doi.org/10.3891/acta.chem.scand.46-0761

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