Enantioselective preparation of 2′,3′-dideoxynucleosides and their analogues from ring-expansion of cyclobutanones. 2. Synthesis of 2′,3′-dideoxyribosides and (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1547-1550

  Lee Ruff, Edward ^a   Xi, Feng De ^a   Qie, Jiang Hua ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE; ANTIVIRUS AGENT;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS; TECHNIQUE;

EID: 0029976296     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9517151     Document Type: Article

References (29)

1. For part 1 see: Lee-Ruff, E.; Wan, W.-Q.; Jiang, J.-L. J. Org. Chem 1994, 59, 2114.
2. Hertel, L. W.; Kroin, J. S.; Misner, J. W.; Tustin, J. M. J. Org Chem. 1988, 53, 2406.
3. Chou, T. S.; Heath, P. C.; Patterson. L. E.; Poteet, L. M.; Lakin, R. E.; Hunt, A. H. Synthesis 1992, 565.
4. Robins, R. K.; Revankar, G. R. in Antiviral Drug Development; De Clercq, E., Walker, R. T., Eds.; Plenum Press: New York, 1988; p 11.
5. Mitsuya, H.; Yarchoan, R.; Broder, S. Science 1990, 249, 1533 and references cited therein.
6. (a) Marquez, V. E.; Lim, M.-I. Med. Res. Rev. 1986, 611.
7. (b) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
8. (c) Niitsuma, S.; Ichikawa, Y.-I.; Takita, T. Studies in Natural Products Chemistry; Elsevier Science Publishers: Amsterdam, 1992; p 585.
9. (a) Manchand, P. S.; Belica, P. S.; Holman, M. J.; Huang, T.-N.; Maehr, H. Tarn, S. Y.-K; Yang, R. T. J. Org. Chem. 1992, 57, 3473.
10. (b) Beach, J. W.; Kim, H. O.; Jeong, L. S.; Nampalli, S.; Islam, Q.; Ahn, S. K.; Babu, J. R.; Chu, C. K. Ibid. 1992, 57, 3887.
11. Svannson, L.; Kvarnström, I.; Classon, B.; Samuelsson, B. J. Org. Chem. 1991, 56, 2993.
12. Lee-Ruff, E. In Methods in Organic Chemistry; De Meijere, A., Ed.; Houben-Weyl; G. Thieme Verlag: Stuttgart, Chapter 1.3, Vol. E17 (in press).
13. Lee-Ruff, E. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; G. Thieme Verlag: Stuttgart, 1991; Vol. 1, p 167.
14. Hayes, I. E. E.; Jandrisits, L.; Lee-Ruff, E. Can. J. Chem. 1989, 67, 2057.
15. (a) Boumchita, H.; Legraverend, M.; Bisagni, E. Heterocycles 1991, 32, 1785.
16. (b) Rosenquist, A.; Kvarnström, I.; Svensson, S. C. T.; Classon, B.; Sammuelsson, B. J. Org. Chem. 1994, 59, 1779.
17. (c) Park, K. H.; Rapoport, H. J. Org. Chem. 1994, 59, 394.
18. (a) Bergmeier, S. C.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1993, 58, 5019.
19. (b) Bergmeier, S. C.; Cobas, A. A.; Rapoport, H. J. Org. Chem. 1993, 58, 2369.
20. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
21. Narasaka, K.; Kusama, H.; Hayashi, Y. Bull Chem. Soc. Jpn. 1991, 64, 1471.
22. Burns, C. L.; St. Clair, M. H.; Frick, L. W.; Spector, T.; Averett, D. R.; English, M. L.; Holmes, T. J.; Krenitsky, T. A.; Koszalka, G. W. J. Org. Chem. 1993, 36, 378.
23. Chu, C. K.; Ullas, G. V.; Jeong, L. S.; Ahn, S. K.; Doboszewski, B.; Lin, Z. X.; Beach, J. W.; Schinazi, R. F.; J. Med. Chem. 1990, 33, 1553
24. Hronowshi, L. J. J.; Szarek, W. A. Can. J. Chem. 1988, 66, 61.
25. Schinazi, R. F. et al. Antimicrob. Agents Chemother 1994, 38, 2172.
26. Lin, T. S. et. al. Biochem. Pharmacol. 1994, 47, 171.
27. Gosselin G. et al. Antimicrob. Agents Chemother. 1994, 38, 1292.
28. Lin, T. S.; Luo, M.-Z.; Liu, M. C. Tetrahedron Lett. 1994, 35, 3477.
29. Kaya, R.; Beller, N. R. J. Org. Chem. 1981, 46, 196.