Browse > Article
http://dx.doi.org/10.5012/bkcs.2004.25.2.221

Enantiomeric Synthesis of Novel Apiosyl Nucleosides as Potential Antiviral Agents  

Kim, Ai-Hong (College of Pharmacy, Chosun University)
Hong, Joon-Hee (College of Pharmacy, Chosun University)
Publication Information
Bulletin of the Korean Chemical Society / v.25, no.2, 2004 , pp. 221-225 More about this Journal
Abstract
A series of 2',3'-dideoxy-3'-fluoro-D-apiosyl nucleosides 15, 16, 17 and 18 were synthesized enantiomerically with L-Gulonic- ${\gamma}$-lactone as the starting material. The reduction of butenolide 1 with DIBAL-H followed by the Luche procedure afforded the allylic alcohol 2. Ozonolysis and the reduction of compound 4 induced the cyclized lactol, which was acetylated to give the acetate 7. Condensation of the acetate 7 with silylated pyrimidine ($N^4$-benzoyl cytosine) and a purine base (6-chloropurine) under Vorbruggen conditions and deblocking afforded a series of fluorinated apiosyl nucleosides.
Keywords
Apiosyl nucleosides; Claisen rearrangement; Luche procedure; Antiviral agents;
Citations & Related Records

Times Cited By Web Of Science : 2  (Related Records In Web of Science)
Times Cited By SCOPUS : 2
연도 인용수 순위
1 Yarchoan, R.; Thomas, R. V.; Allain, J.-P.; McAtee, N.; Dubinsky,R.; Mitsuya, H.; Lawley, T. J.; Safai, B.; Myers, C. E.; Perno, C.F.; Klecker, R. W.; Wills, R. J.; Fischl, M. A.; McNeely, M. C.;Pluda, J. M.; Leuther, M.; Collins, J. M.; Broder, S. Lancet 1988,1, 76.
2 Lin, T.-S.; Schinazi, R. F.; Prusoff, W. H. Biochem. Pharmacol.1987, 36, 2713.   DOI   ScienceOn
3 Herdewijn, P.; Balzarini, J.; De Clerq, E.; Pauwels, R.; Baba, M.; Broder, S.; Vanderhaeghe, H. J. Med. Chem. 1987, 30, 1270   DOI
4 Ojima, I.; McCarty, J. R.; Welch, J. T. In ACS Symposium Series; Amercan Chemical Society: Washington, DC, 1996; p 639.
5 Biggadike, K.; Borthwick, A. D. J. Chem. Soc., Chem. Commun. 1990, 1380.
6 Furman, P. A.; Fyfe, J. A.; St. Clair, M. H.; Weinhold, K.; Rideout,J. L.; Freeman, G. A.; Nusinoff-Lehrman, S.; Bolognesi, D. P.;Broder, S.; Mitsuya, H.; Barry, D. W. Proc. Natl. Acad. Sci. U.S.A.1986, 83, 8333.   DOI   ScienceOn
7 Schinazi, R. F.; Chu, C. K.; Peck, A.; McMillan, A.; Mathis, R.;Cannon, D.; Jeong, L. S.; Beach, J. W.; Choi, W. B.; Yeola, S.;Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 672.   DOI   ScienceOn
8 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.
9 Maag, H.; Rydzewski, R. M.; McRoberts, M. J.; Crawford- Ruth, D.; Verheyden, J. P. H.; Prisbe, E. J. J. Med. Chem. 1992, 35, 1440   DOI
10 Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065.
11 De Clerq, E. Anticancer Res. 1987, 7, 1023.
12 Ahn, S. K.; Kim, D.; Son, H. J.; Jeong, B. S.; Hong, R. K.; Kim,B. Y.; Kim, E. N.; Chung, K. H.; Kim, J. W. J. Chem. Soc., Chem.Commun. 1998, 967.
13 Molander, G. A. Chem. Rev. 1992, 92, 29.   DOI
14 Welch, J. T. Tetrahedron 1987, 43, 3123   DOI   ScienceOn
15 Watanabe, K. A.; Harada, K.; Zeidler, J.; Matulic-Adamic, J.; Takahashi, K.; Ren, W.-Y.; Cheng, Y.-C.; Fox, J. J.; Chou, T.-C.; Zhu, Q.-Y.; Polsky, B.; Gold, J. W. M.; Armstrong, D. J. Med. Chem. 1990, 33, 2145   DOI
16 Tann, C. H.; Brodfuehrer, P. R.; Brundidge, S. P.; Sapino, C.; Howell, H. G. J. Org. Chem. 1985, 50, 3644.   DOI
17 Lee, K.; Choi, Y.; Gullen, E.; Wirtz, S. S.; Schinazi, R. F.; Cheng,Y. C.; Chu, C. K. J. Med. Chem. 1999, 42, 1320.   DOI   ScienceOn
18 Patrick, T. B.; Lanahan, M. V.; Yang, C.; Walker, J. K.; Hutchinson, C. L.; Neal, B. E.; J. Org. Chem. 1994, 59, 1210   DOI   ScienceOn
19 Choi, Y.; Lee, K.; Hong, J. H.; Schinazi, R. F.; Chu, C. K.Tetrahedron Lett. 1998, 39, 4437.   DOI   ScienceOn
20 Hong, J. H.; Lee, K.; Choi, Y.; Chu, C. K. Tetrahedron Lett. 1998,39, 3443.   DOI   ScienceOn
21 Yarchoan, R.; Mitsuya, H.; Thomas, R. V.; Pluda, J. M.; Hartman,N. R.; Perno, C. F.; Marczyk, K. S.; Allain, J.-P.; Johns, D. G.;Broder, S. Science 1989, 245, 412.   DOI   ScienceOn