Selective ring-opening fluorination of epoxide: An efficient synthesis of 2'-C-Fluoro-2'-C-methyl carbocyclic nucleosides

Bulletin of the Korean Chemical Society

Volumn 30, Issue 12, 2009, Pages 2989-2992

  Liu, Lian Jin ^a   Kim, Si Wouk ^a   Lee, Wonjae ^a   Hong, Joon Hee ^a  

^a Chosun University   (South Korea)

Author keywords

Anti HCV agent; Carbocyclic nucleoside; Fluorohydrin; Mitsunobu reaction

Indexed keywords

CARBOCYCLIC NUCLEOSIDES; DEPROTECTION; EFFICIENT SYNTHESIS; EPOXIDE INTERMEDIATE; FLUOROHYDRIN; HEPATITIS C VIRUS; HUH-7 CELLS; IN-VITRO; MITSUNOBU REACTIONS; RING OPENING; SYNTHETIC ROUTES;

BIOMOLECULES; CELL CULTURE; FLUORINE; VIRUSES;

SYNTHESIS (CHEMICAL);

EID: 76649144180     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2009.30.12.2989     Document Type: Article

References (18)

1. Tan, S. L.; Pause, A.; Shi, Y.; Sonenberg, N. Nat. Rev. Drug Discovery 2002, 1, 867-881.
2. Heathcote, E.; Shiffman, M.; Cooksley, W.; Dusheiko, G. M.; Lee, S. S.; Balart, L.; Reindollar, R.; Reddy, R. K.; Wright, T. L.; Lin, A.; Hoffman, J.; De Pamphilis, J. N. Engl. J. Med. 2000, 343, 1673-1680.
3. Clark, J. L.; Hollecker, L.; Mason, J. C.; Stuyver, L. J.; Tharnish, P. M.; Lostia, S.; McBrayer, T. R.; Schinazi, R. F.; Watanabe, K. A.; Otto, M. J.; Furman, P. A.; Stec, W. J.; Patterson, S. E.; Pankiewicz, K. W. J. Med. Chem. 2005, 48, 5504-5508.
4. Smith, D. B. Kalayanov, G.; Sund, C.; Winqvist, A.; Pinho, P.; Maltseva, T.; Morisson, V.; Leveque, V.; Rajyaguru, S.; Le Pogam, S.; Najera, I.; Benkestock, K.; Zhou, X. X.; Maag. H.; Cammack, N.; Martin, J. A.; Swallow, S.; Johansson, N. G.; Klumpp, K.; Smith, M. J. Med. Chem. 2009, 52, 219-223
5. Li, H.; Baik, Y. C.; Hong, J. H. Bull. Korean Chem. Soc. 2009, 30, 1147-1151.
6. El Kouni, M. H. Curr. Pharm. Des. 2002, 8, 581-593.
7. Carrol, S. S.; Tomassini, J. E.; Bosserman, M.; Getty, K.; Stahlhut, M. W.; Eldrup, A. B.; Bhat, B.; Hall, D.; Simcoe, A. L.; LaFemina, R.; Rutkowski, C. A.; Wolanski, B.; Yang, Z.; Migliaccio, G.; De Francesco, R.; Kuo, L. C.; MacCross, M.; Olsen, D. B. J. Biol. Chem. 2003, 278, 11979-11984.
8. Eldrup, A. B.; Allerson, C. R.; Bennett, C. F.; Bera, S.; Bhat, B.; Bhat, N.; Bosserman, M. R.; Brooks, J.; Burlein, C.; Carrol, S. S.; Cook, P. D.; Getty, K. L.; MacCross, M.; McMasters, D. R.; Olsen, D. B.; Prakash, T. P.; Prhavc, M.; Song, Q. L.; Tomassini, J. E.; Xia, J. J. Med. Chem. 2004, 47, 2283-2295.
9. Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571-623
10. Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768
11. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670
12. Crimmins, M. T. Tetrahedron 1998, 54, 9229-9272
13. Ariona, O.; Gómez, A. M.; López, J. C.; Plumet, J. Chem. Rev. 2007, 107, 1919-2036.
14. Gosselin, G.; Criffe, L.; Meillon, J.-C.; Storer, R. Tetrahedron 2006, 62, 906-914.
15. Shimizu, M.; Nakahara, Y. J. Fluorine Chem. 1999, 99, 95-97.
16. Kitade, Y.; Ando, T.; Yamaguchi, T.; Hori, A.; Nakanishi, M.; Ueno, Y. Bioorg. Med. Chem. 2006, 14, 5578-5583.
17. Michel, B. Y.; Strazewski, P. Tetrahedron 2007, 63, 9836-9841.
18. Kim, H. J.; Sharon, A.; Bal, C.; Wang, J.; Allu, M.; Huang, Z.; Murray, M. G.; Bsaait, L.; Schinazi, R. F.; Korba, B.; Chu, C. K. J. Med. Chem. 2009, 52, 206-213.