Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Novel Mercaptophenyl Carbocyclic C-Nucleoside Analogue Using Sequential [3,3]-Sigmatropic Rearrangement and Ring-closing Metathesis

  • Li, Hua (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK-21 Project Team, College of Pharmacy, Chosun University)
  • Published : 2008.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Novel mercaptophenyl carbocyclic C-nucleoside analogue was synthesized via a cyclopentenol intermediate 10, which was prepared using a sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM). Friedel-Crafts alkylation was then used to couple the thiophenol.

Keywords

References

  1. Breslauer, K. J.; Frank, R.; Blocker, H.; Marky, L. A. Proc. Acad. Sci. USA 1986, 83, 3745
  2. SantaLucia, J.; Allawi, H. T.; Seneviratne, P. A. Biochemistry 1996, 35, 3555 https://doi.org/10.1021/bi951907q
  3. Ren, K. F.; Schweitzer, B. A.; Sheils, C. J.; Kool, E. T. Angew. Chem. Int. Ed. Engl. 1996, 35, 743 https://doi.org/10.1002/anie.199607431
  4. Wang, H.; Osborne, S. E.; Zuiderweg, E. R. P.; Glick, G. D. J. Am. Chem. Soc. 1994, 116, 5021 https://doi.org/10.1021/ja00090a071
  5. Osborne, S. E.; Volker, J.; Stevens, S. Y.; Breslauer, K. J.; Glick, G. D. J. Am. Chem. Soc. 1996, 118, 11993 https://doi.org/10.1021/ja962386c
  6. Kool, E. T. Biopolymers 1998, 48, 3 https://doi.org/10.1002/(SICI)1097-0282(1998)48:1<3::AID-BIP2>3.0.CO;2-7
  7. Roberts, C.; Bandaru, R.; Switzer, C. J. Am. Chem. Soc. 1997, 119, 4640 https://doi.org/10.1021/ja970123s
  8. Parsch, J.; Engels, J. W. J. Am. Chem. Soc. 2002, 124, 5664 https://doi.org/10.1021/ja012116g
  9. Matray, T. J.; Kool, E. T. Nature 1999, 399, 704 https://doi.org/10.1038/21453
  10. Liu, H.; Lynch, S. R.; Kool, E. T. J. Am. Chem. Soc. 2004, 126, 6900 https://doi.org/10.1021/ja0497835
  11. Liu, H.; Gao, J.; Lynch, S. R.; Saito, Y. D.; Maynard, L. Y.; Kool, E. T. Science 2003, 302, 868 https://doi.org/10.1126/science.1088334
  12. Herdewijn, P.; De Clercq, E.; Balzarini, J.; Vanderhaeghe, H. J. Med. Chem. 1985, 28, 550 https://doi.org/10.1021/jm50001a003
  13. Chun, B. K.; Song, G. Y.; Chu, C. K. J. Org. Chem. 2001, 66, 4852 https://doi.org/10.1021/jo010224f
  14. Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571 https://doi.org/10.1016/S0040-4020(01)88122-9
  15. Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745 https://doi.org/10.1021/cr00016a004
  16. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611 https://doi.org/10.1016/S0040-4020(01)89258-9
  17. Crimmins, M. T. Tetrahedron 1998, 54, 9229 https://doi.org/10.1016/S0040-4020(98)00320-2
  18. Ariona, O.; Gomez, A. M.; López, J. C.; Plumet, J. Chem. Rev. 2007, 107, 1919 https://doi.org/10.1021/cr0203701
  19. Hong, J. H.; Lee, K.; Choi, Y.; Chu, C. K. Tetrahedron Lett. 1998, 39, 3443 https://doi.org/10.1016/S0040-4039(98)00567-X
  20. Hong, J. H.; Gao, M. Y.; Chu, C. K. Tetrahedron Lett. 1999, 40, 231 https://doi.org/10.1016/S0040-4039(98)02324-7
  21. Hong, J. H.; Gao, M. Y.; Choi, Y. S.; Cheng, Y.-C.; Schinazi, R. F.; Chu, C. K. Carbohydr. Res. 2000, 328, 37 https://doi.org/10.1016/S0008-6215(00)00005-7
  22. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413 https://doi.org/10.1016/S0040-4020(97)10427-6
  23. Philips, A, J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75
  24. Furstner, A. Angew. Chem. Int. Ed. 2000, 38, 3012
  25. Seepersaud, M.; Al-Abed, Y. Tetrahedron Lett. 2000, 41, 7801 https://doi.org/10.1016/S0040-4039(00)01355-1
  26. Gillaizeau, I.; Charamon, S.; Agrofoglio, L. A. Tetrahedron Lett. 2001, 42, 8817 https://doi.org/10.1016/S0040-4039(01)01905-0
  27. Kim, A.; Hong, J. H. Bull. Korean Chem. Soc. 2005, 26, 1767 https://doi.org/10.5012/bkcs.2005.26.11.1767
  28. Oh, C. H.; Hong, J. H. Bull. Korean Chem. Soc. 2005, 26, 1520 https://doi.org/10.5012/bkcs.2005.26.10.1520
  29. Hatano, A.; Makita, S.; Kirihara, M. Tetrahedron 2005, 61, 1723 https://doi.org/10.1016/j.tet.2004.12.038

Cited by

  1. ChemInform Abstract: Synthesis of Novel Mercaptophenyl Carbocyclic C-Nucleoside Analogue (XII) Using Sequential [3,3]-Sigmatropic Rearrangement and Ring-Closing Metathesis. vol.39, pp.36, 2008, https://doi.org/10.1002/chin.200836205
  2. Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji–Trost coupling vol.12, pp.None, 2008, https://doi.org/10.3762/bjoc.12.107