Efficient synthesis of carbocyclic nucleoside, (±)-homocarbovir via π- allylpalladium complex formation from the allyl N,N-ditosylimide substrate

Nucleosides, Nucleotides and Nucleic Acids

Volumn 19, Issue 3, 2000, Pages 619-628

  Rhee, Hakjune ^a   Yoon, Dong Oh ^a,c   Jung, Michael E ^b  

^a Hanyang University   (South Korea)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c C and C Research Laboratories   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CARBOCYCLIC NUCLEOSIDE; CARBOVIR; PALLADIUM COMPLEX;

ACETYLATION; ANALYTIC METHOD; ARTICLE; BIOAVAILABILITY; CATALYSIS; COMPLEX FORMATION; COUPLING FACTOR; CYTOTOXIC T LYMPHOCYTE; DERIVATIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; T LYMPHOCYTE ACTIVATION;

EID: 0034000205     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257770008035012     Document Type: Article

References (26)

1. (a) Marquez, V. E.; Lim, M. I. Med. Res. Rev. 1986, 6, 1-40.
2. (b) Hobbs, J. B. In Comprehensive Medicinal Chemistry; Hansch, C.; Sammers, P. G.; Taylor, J. B., Eds.; Pergamon; Oxford, 1990; Vol. 2, pp 306-322.
3. (c) Hovi, T. In Antiviral Agents: The Development and Assassment of Antiviral Chemotherapy; Field, H. J., Ed.; CRC Press; 1988; Chapter 1, pp 1-12.
4. (a) Daluge, S. M. U.S. Patent 5,034,394, 1991.
5. (b) Kimberlin, D. W.; Coen, D. M.; Biron, K. K.; Cohen, J. I.; Lamb, R. A.; McKlinlay, M.; Emini, E. A.; Whitley, R. J. Antiviral Res. 1995, 26, 369-401.
6. (c) Daluge, S. M.; Good, S. S.; Faletto, M. B.; Miller, W. H.; Clair, M. H. S.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J. E.; Dornsife, R. E.; Averett, D. R.; Krenitsky, T. A. Antimicrobial Agents and Chemotherapy 1997, 41, 1082-1093.
7. (d) Faletto, M. B.; Miller, W. H.; Garvey, E. P.; Clair, M. H. S.; Daluge, S. M.; Good, S. S. Antimicrobial Agents and Chemotherapy 1997, 41, 1099-1107.
8. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3739-3747.
9. (a) Akella, L. B.; Vince, R. Tetrahedron 1996, 52, 2789-2794.
10. th Annual Meeting of the Korean Chemical Society, Poster Session, 1996.
11. (c) Olivo, H. F.; Yu, J. Tetrahedron: Asymmetry 1997, 8, 3785-3788.
12. (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20.
13. (b) Tsuji, J. Tetrahedron 1986, 42, 4361-4401.
14. (a) Trost, B. M.; Kuo, G.-H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621-622.
15. (b) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747.
16. (a) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074.
17. (b) Roberts, S. M.; Shoberu, K. A. J. Chem. Soc., Perkin Trans. 1 1991, 2605-2607.
18. (c) Gundersen, L.-L.; Benneche, T.; Undheim, K. Tetrahedron Lett. 1992, 33, 1085-1088.
19. (a) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720.
20. (b) Katagiri, N.; Takebayashi, M.; Kokufuda, H.; Kaneko, C.; Kanehira, K.; Torihara, M. J. Org. Chem. 1997, 62, 1580-1581.
21. Rhee, H.; Yoon, D.; Kim, S. Bull. Korean Chem. Soc. 1998, 19, 25-27.
22. (a) Oehlschlager, A. C.; Zalkow, L. H. J. Chem. Soc., Chem. Commun. 1965, 70-71.
23. (b) Oehlschlager, A. C.; Zalkow, L. H. J. Org. Chem. 1965, 30, 4205-4211.
24. 1H NMR spectrum (Two allylic protons at C-4′ show up at 2.66 ppm).
25. Still, W. C.; Kahn, M.; Mitra, A. J.Org. Chem. 1978, 43, 2923-2925.
26. Armarego, W. L. F.; Perin, D. D. Purification of Laboratory Chemicals, 4th Edition, Butterworth-Heinemann, 1996.