Synthesis of 4′-thionucleosides by 1,3-dipolar cycloadditions of the simplest thiocarbonyl ylide with alkenes bearing electron-withdrawing groups

Tetrahedron Letters

Volumn 48, Issue 28, 2007, Pages 4915-4918

  Corsaro, Antonino ^a   Pistarà, Venerando ^a   Chiacchio, Maria Assunta ^a   Vittorino, Elisa ^a   Romeo, Roberto ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

Author keywords

1,3 Dipolar cycloaddition; Antiviral; Thiocarbonyl ylide; Thionucleosides

Indexed keywords

ALKENE DERIVATIVE; AMIDE; CARBONYL DERIVATIVE; CYTOSINE DERIVATIVE; FLUOROURACIL DERIVATIVE; FUMARIC ACID DIMETHYL ESTER; HYDROXYL GROUP; MALIC ACID DERIVATIVE; NUCLEOSIDE DERIVATIVE; THYMINE DERIVATIVE; URACIL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CYCLOADDITION; DEPROTECTION REACTION; DIPOLE; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 34250017432     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.080     Document Type: Article

References (36)

1. For reviews see:. Huryn D.M. Chem. Rev. 92 (1992) 1745-1768
2. De Clercq E. Nucleosides and Nucleotides 13 (1994) 1271-1295
3. Yokoyama M. Synthesis (2000) 1637-1655
4. Gumina G., Olgen S., and Chu C.K. In: Chu C.K. (Ed). Antiviral Nucleosides. Chiral Synthesis and Chemotherapy (2003), Elsevier, New York 77-189
5. Gumina G., Copperwood J.S., and Chu C.K. In: Chu C.K. (Ed). Antiviral Nucleosides. Chiral Synthesis and Chemotherapy (2003), Elsevier, New York 191-258
6. Merino P. Curr. Med. Chem. 13 (2006) 539-545
7. Reist E.J., Goodman L., Lee W.W., Baker B.R., and Benitez A. J. Org: Chem. 27 (1962) 3274-3279
8. Parks R., Stoeckler J., Cambor C., Savarese T., Crabtree G., and Chu S. In: Sartorelli A., Lazo T., and Bertino J. (Eds). Molecular Actions and Targets for Cancer Chemotherapeutic Agents (1981), Academic Press, New York 229
9. Paulsen H., and Todt K. Adv. Carbohydr. Chem. 23 (1968) 115-232
10. Dyson M.R., Coe P.L., and Walker R.T. Carbohyd. Res. 216 (1991) 237-248
11. Bredenkamp M.W., Holzapfel C.W., and Swanepoel A.D. Tetrahedron Lett. 31 (1990) 2759-2762
12. Bellon L., Barascut J.L., and Imbach J.L. Nucleosides Nucleotides 11 (1992) 1467-1479
13. Rassu G., Spanu P., Pinna L., Zanardi F., and Casiraghi G. Tetrahedron Lett. 36 (1995) 1941-1944
14. Choi Y., Choo H., Chong Y., Lee S., Olgen S., Schinazi R.F., and Chu C.K. Org. Lett. 4 (2002) 305-307
15. Chu C.K., Choi Y., Choo H., Chong Y., Lee S., Zhu W., and Schinazi R.F. Antiviral Res. 53 (2002) A36
16. Taguchi Y., and Suhara Y. Bull. Chem. Soc. Jpn. 59 (1986) 2321-2324
17. Pederson R.L., Liu K.K.C., Rutan J.F., Chen L., and Wong C.-H. J. Org. Chem. 55 (1990) 4897-4901
18. Romeo G., Iannazzo D., Piperno A., Romeo R., Corsaro A., Rescifina A., and Chiacchio U. Mini-Rev. Org. Chem. 2 (2005) 59
19. For a review, see:. Kellog R.M. Tetrahedron 32 (1976) 2165
20. Hosomi A., Matsuyama Y., and Sakurai H. J. Chem. Soc., Chem. Commun. (1986) 1073
21. 4-hydroxymethyl group.
22. Kita Y., Yasuda H., Tamura O., Itoh F., and Tamura Y. Tetrahedron Lett. 25 (1984) 4681-4682
23. Kita Y., Tamura O., Yasuda H., Itoh F., and Tamura Y. Chem. Pharm. Bull. 33 (1985) 4235-4241
24. Naka T., Minakawa N., Abe H., Kaga D., and Matsuda A. J. Am. Chem. Soc. 122 (2000) 7233-7243 and references cited therein
25. Naka T., Nishizono N., Minakawa N., and Matsuda A. Tetrahedron Lett. 40 (1999) 6297-6300 and references cited therein
26. Karlson S., and Högberg H.-E. Org. Lett. 1 (1999) 1667-1679
27. Vedejis E., and Martinez G.R. J. Am. Chem. Soc. 102 (1980) 7993-7994
28. Vedejis E., and Martinez G.R. J. Am. Chem. Soc. 101 (1979) 6452-6454
29. Walter L.A., Goodson L.H., and Fosbinder R.J. J. Am. Chem. Soc. 67 (1945) 655-657
30. Kikuchi Y., Kurata H., Nishiyama S., Yamamura S., and Kato K. Tetrahedron Lett. 38 (1997) 4795-4798
31. Nicolaou K.C., Papahatjis D.P., Clameron D.A., Magolda R.L., and Dolle R.E. J. Org. Chem. 50 (1985) 1440-1456
32. Aono M., Terao Y., and Achiwa K. Heterocycles 24 (1986) 313-315
33. Jung M.E., and Kretschik O. J. Org. Chem. 63 (1998) 2975-2981
34. 1H NOE experiments on the same compounds, with the exception of 5-F-uracil, reported by Jeong and co-workers (see Ref. 25).
35. Haraguchi K., Takahashi H., Shiina N., Horii C., Yoshimura Y., Nishikawa A., Sasakura E., Nakamura K.T., and Tanaka H. J. Org. Chem. 67 (2002) 5919-5927
36. Moon H.R., Kim H.O., Lee S.K., Choi W.J., Chun M.W., and Jeong L.S. Bioorg. Med. Chem. 10 (2002) 1499