Synthesis of novel spiro[2.3]hexane carbocyclic nucleosides via enzymatic resolution

Organic Letters

Volumn 6, Issue 15, 2004, Pages 2531-2534

  Bondada, Lavanya ^a   Gumina, Giuseppe ^a   Nair, Ranjeet ^a   Xing, Hai Ning ^a   Schinazi, Raymond F ^b   Chu, Chung K ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b ATLANTA VA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9 (6 HYDROXYMETHYLSPIRO[2.3]HEXANE) 4 ADENINE; ACETIC ACID; ADENINE DERIVATIVE; ALCOHOL; ALKENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIETHOXYKETENE; FUMARIC ACID DERIVATIVE; FUMARIC ACID DIETHYL ESTER; NUCLEOSIDE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; BURKHOLDERIA CEPACIA; ENZYME SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; ULTRAVIOLET RADIATION;

ACETATES; ALCOHOLS; BURKHOLDERIA CEPACIA; CATALYSIS; FUMARATES; HEXANES; LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEOSIDES;

EID: 4043086482     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0491989     Document Type: Article

References (25)

1. (a) Antiviral nucleosides: Chiral Synthesis and Chemotherapy, Chu, C. K., Eds.; Elsevier: New York, 2003.
2. (b) Recent advances in nucleosides: Chemistry and Chemotherapy; Chu, C. K., Ed.; Elsevier: New York, 2002.
3. Shimada, N.; Hasegawa, S.; Harada, T.; Tomosawa, T.; Fujji, A.; Takita, T. J. Antibiot. 1986, 39, 1623-1625.
4. Hoshino, H.; Shimizu, N.; Shimada, M.; Tokito, T.; Takeuchi, T.; J. Antibiot. 1986, 39, 1077-1078.
5. Honjo, M.; Maruyama, T.; Sato, Y.; Morii, T. Chem. Pharm. Bull. 1989, 37, 1413-1416.
6. (a) Norbeck, D. W.; Kern, E.; Hayashi, S.; Rosenbrook, W.; Sham, H.; Henin, T.; Plattner, J. J.; Erickson, J.; Clement, J.; Shannon, W.; Shipkowitz, N.; Hardy, D.; Marsh, K.; Arnett, G.; Shannon, W.; Broder, S.; Mitsuya, H. J. Med. Chem. 1990, 33, 1281-1285.
7. (b) Maruyama, T.; Hanai, Y.; Sato, Y.; Snoeck, R.; Andrei, G.; Hosoya, M.; Balzarini, J.; Clercq, E. D. Chem. Pharm. Bull. 1993, 41, 516-521.
8. (a) Somekawa, K.; Hara, R.; Kinnami, K.; Muraoka, S. T.; Shimo, T. Chem. Lett. 1995, 407-408.
9. (b) Bisacchi, G. S.; Singh, J.; Godfrey, J. D., Jr.; Kissick, T. P.; Mitt, T.; Malley, M. F.; Di Marco, J. D.; Gougoutas, J. Z.; Mueller, R. H.; Zahler, R. J. Org. Chem. 1995, 60, 2902-2905.
10. (c) Maruyama, T.; Hanai, Y.; Sato. Y. Nucleosides Nucleotides. 1992, 11, 855-864.
11. (d) Maruyama, T.; Hanai, Y.; Sato. Y.; Snoeck, R.; Andrei, G.; Hosoya, M.; Balzarini, J.; Clercq, D. Chem. Pharm. Bull. 1993, 41, 516-521.
12. (e) Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Chem. Pharm. Bull 1990, 38, 2719-2725.
13. Guan, H. P.; Ksebati, M. B.; Cheng, Y. C.; Drach, J. C.; Kern, E.; Zemlicka, J. J. Org. Chem. 2000, 65, 1280-1290.
14. Jones, B. C. N. M.; Drach, J. C.; Corbett, T. H.; Kessel, D.; Zemlicka, J. J. Org. Chem. 1995, 60, 6277-6287.
15. (a) Wang, P.; Gullen, B.; Newton, M. G., Cheng, Y. C.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 1999, 42, 3390-3399.
16. (b) Wang, P.; Agrofoglio, L. A.; Newton, H. G.; Chu, C. K. J. Org. Chem. 1999, 64, 4173-4178.
17. Bisacchi, G. S.; Braitman, A.; Cianci, C. W.; Clark, J. M.; Field, A. K.; Hagen, M. E.; Hockstein, D. R.; Malley, M. F.; Mitt, T.; Slusarchyk, W. A.; Sundeen, J. E.; Terry, B. J.; Tuomari, A. V.; Weaver, E. R.; Young, M. G.; Zahler, R. J. Med. Chem. 1991, 34, 1415-1421.
18. Ichikawa, Y.; Narita, A.; Shiozawa, A.; Hayashi, Y.; Narasaka, K. J. Chem. Soc., Chem. Commun. 1989, 43, 1919-1921.
19. Jung, M. E.; Sledeski, A. W. J. Chem. Soc., Chem. Commun. 1993, 589-591.
20. (a) Slusarchyk, W. A.; Young, M. G.; Bisacchi, G. S.; Hockstein. D. R.; Zahler, R. Tetrahedron Lett. 1989, 30, 6453-6456.
21. (b) Brannock, K. C.; Burpitt, R. D.; Thweatt, J. G. J. Org. Chem. 1964, 29, 940.
22. 6 (p-nitrobenzoyl derivative): C, 60.28; H, 5.37; N, 4.39. Found: C, 60.36; H, 5.68; N, 4.19.
23. 5O: C, 58.76; H, 6.16; N, 28.55. Found: C, 58.62; H, 6.20; N, 28.30.
24. 5O: C, 58.76; H, 6.16; N, 28.55. Found: C, 58.34; H, 6.14; N, 28.01.
25. Schinazi, R. F.; Sommadossi, J. P.; Saalmann, V.; Cannon, D. L.; Xie, M. W.; Hart, G. C.; Smith, G. A.; Hahn, E. F. Activity of 3′-azido-3′- deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 1990, 34, 1061-1067.