Enantioselective synthesis of isoxazolidinyl thymine and cytosine nucleosides

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4877-4880

  Xiang, Yuejun ^a   Gong, Youxiang ^a   Zhao, Kang ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; GAMMA LACTONE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; METHOXYAMINE; NUCLEOSIDE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; HUMAN IMMUNODEFICIENCY VIRUS 1; POLYMERIZATION; STEREOSPECIFICITY;

EID: 0030575415     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00999-9     Document Type: Article

References (22)

1. 1. For selected reviews of antiviral nucleoside chemistry, see: (a) Marquez, V. E.; Lim, M.-I. Med. Res. Rev. 1986, 6, 1.
2. (b) Qinkert, G. Synform 1989, 7, 225.
3. (c) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
4. (d) De Clercq, E. AIDS Res. Humn. Retroviruses 1992, 8, 119.
5. (e) De Clercq, E. Nucleosides Nucleotides 1994, 13, 1271.
6. (f) Nair, V.; Jahnke, T. S. Antimicrob. Agents Chemother. 1995, 39, 1017.
7. 2. For selected recent examples, see: (a) Lin, T.-S.; Luo, M.-Z.; Liu, M.-C.; Tertrahedron 1995, 51, 1055.
8. (b) Liang, C.; Lee, D. W.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 1546.
9. (c) Jin, H.; Siddiqui, M. A.; Evans, C. A.; Tse, H. L. A.; Mansour, T. S. J. Org. Chem. 1995, 60, 2621.
10. (d) Jeong, L. S.; Marquez, V. E. J. Org. Chem. 1995, 60, 4276.
11. 3. Xiang, Y.; Chen, J.; Schinazi, R. F.; Zhao, K. Tetrahedron Lett. 1995, 36, 7193.
12. 4. Xiang, Y.; Chen, J.; Schinazi, R. F.; Zhao, K. Bioorg. Med. Chem. Lett. 1996, in press.
13. 5. For examples of the racemic synthesis of isoxazolidinyl nucleosides, see references 3, 4 and (a) Tronchet, J. M. J.; Iznaden, M.; Barbalat-Rey, F.; Dhimane, H.; Ricca, A.; Balzarini, J.; De Clercq, E. Eur, J. Med. Chem. 1992, 27, 555.
14. (b) Tronchet, J. M. J.; Iznaden, M.; Barbalat-Rey, F.; Komaromi, I.; Dolatshahi, N.; Berbardinelli, G. Nucleosides Nucleotides 1995, 14, 1737.
15. 6. For the related examples, see: (a) Maciejewski, S.; Panfil, I.; Belzecki, C.; Chemielewski, M. Tetrahedron 1992, 48, 10363.
16. (b) Socha, D.; Jurczak, M.; Chemielewski, M. Tetrahedron Lett. 1995, 36, 135.
17. (c) Collis, M. P.; Hockless, D. C. R.; Perlmutter, P. Tetrahedron Lett. 1995, 36, 7133.
18. 3) δ 6.32 (t, J = 3.6 Hz, 1H, H-5), 4.01 (m, 2H, H-6 and H-7), 3.73 (dd, J = 7.7, 5.0 Hz, 1 H, H-7), 3.13 (dd, J = 6.6, 13.5 Hz, 1H, H-3), 2.83 (s, 3H, N-Me), 2.54 (dd, J = 3.6, 6.8 Hz, 2H, H-4), 2.02 (s, 3H, Ac), 1.38 (s, 3H, Me), 1.29 (s, 3H, Me).
19. 8. For the transition metal-chelated cis glycosylation of oxothiolanyl acetate and trimethylsilylated nucleoside bases, see: Wilson, L. J.; Choi, W.-B.; Spurling, T.; Liotta, D. C.; Schinazi, R. F.; Cannon, D.; Painter, G. R.; St. Clair, M.; Furman, P. A. Bioorg. Med. Chem. Lett. 1993, 3, 169.
20. 3 (Figure).
21. 3OD) δ 169.3; 143.1; 95.7; 85.4; 71.1; 62.6; 45.3; 42.9.
22. 11. A method for the conversion of N-(p-methoxybenzyl)-isoxazolidines to dihydroisoxazoles by DDQ oxidation has been developed and a manuscript is in preparation.