Synthesis of 2,3-dihydro-1,4-dithiinyl nucleosides via Pummerer-type glycosidation

Tetrahedron Letters

Volumn 51, Issue 46, 2010, Pages 6060-6063

  Paolella, Concetta ^a   D'Alonzo, Daniele ^a   Guaragna, Annalisa ^a   Cermola, Flavio ^a   Palumbo, Giovanni ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Dithiins; Heterocyclic nucleosides; Nucleoside analogues; Pummerer type glycosidation

Indexed keywords

4 AMINO 1 [5 (HYDROXYMETHYL) 2,3 DIHYDRO 1,4 DITHIIN 2 YL] 1,2 DIHYDRO 2 PYRIMIDINONE; 4 AMINO 1 [6 (HYDROXYMETHYL) 2,3 DIHYDRO 1,4 DITHIIN 2 YL] 1,2 DIHYDRO 2 PYRIMIDINONE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; GLYCOSIDATION; PUMMERER REACTION; SYNTHESIS;

EID: 77957991059     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.060     Document Type: Article

References (29)

1. P. Herdewijn Modified Nucleosides: In Biochemistry Biotechnology and Medicine 2008 Wiley-VCH GmbH Weinheim
2. G. Gumina, Y. Choi, and C.K. Chu C.H. Chu, Antiviral Nucleosides: Chiral Synthesis and Chemotherapy 2003 Elsevier B.V. Chap 1, pp. 1-76
3. E. Ichikawa, and K. Kato Curr. Med. Chem. 8 2001 385 423
4. G. Romeo, U. Chiacchio, A. Corsaro, and P. Merino Chem. Rev. 110 2010 3337 3370
5. P. Merino Curr. Med. Chem. 13 2006 539 545
6. T.S. Mansour, and R. Storer Curr. Pharm. Design 3 1997 227 264
7. T. Cihlar, and A.S. Ray Antiviral Res. 85 2010 39 58
8. E. De Clercq Future Med. Chem. 2 2010 1049 1053
9. C. Flexner Nat. Rev. Drug Disc. 6 2007 959 966
10. E. De Clercq Nat. Rev. Drug Disc. 1 2002 13 25
11. R. Caputo, A. Guaragna, G. Palumbo, and S. Pedatella Eur. J. Org. Chem. 2003 346 350
12. R. Caputo, A. Guaragna, G. Palumbo, and S. Pedatella Eur. J. Org. Chem. 1999 1455 1458
13. D. D'Alonzo, A. Guaragna, A. Van Aerschot, P. Herdewijn, and G. Palumbo J. Org. Chem. 75 2010 6402 6410
14. D. D'Alonzo, A. Van Aerschot, A. Guaragna, G. Palumbo, G. Schepers, S. Capone, J. Rozenski, and P. Herdewijn Chem. Eur. J. 15 2009 10121 10131
15. D. D'Alonzo, A. Guaragna, A. Van Aerschot, P. Herdewijn, and G. Palumbo Tetrahedron Lett. 49 2008 6068 6070
16. A. Guaragna, S. Pedatella, and G. Palumbo L.A. Paquette, e-Encyclopedia of Reagents for Organic Synthesis (e-EROS) 2008 John Wiley & Sons New York, US
17. A. Guaragna, D. D'Alonzo, C. Paolella, C. Napolitano, and G. Palumbo J. Org. Chem. 75 2010 3558 3568
18. The models were generated by energy minimization with the amber force field of the structures using the HYPERCHEM 8.0 software package (Hypercube Inc.).
19. H. Huang, R. Chopra, G.L. Verdine, and S.C. Harrison Science 282 1998 1669 1675
20. V.E. Marquez, T. Ben-Kasus, J.J. Barchi Jr., K.M. Green, M.C. Nicklaus, and R. Agbaria J. Am. Chem. Soc. 126 2004 543 549
21. S. Eriksson, B. Munch-Petersen, K. Johansson, and H. Eklund Cell. Mol. Life Sci. 59 2002 1327 1346
22. All substrates did not exhibit any reactivity when in situ generated TFDO [methyl(trifluoromethyl)dioxirane] was used.
23. For a thioether oxidation of 5,6-dihydro-1,4-dithiins by photooxygenation, see: F. Cermola, A. Guaragna, M.R. Iesce, G. Palumbo, R. Purcaro, M. Rubino, and A. Tuzi J. Org. Chem. 72 2007 10075 10080
24. E. Wojaczyńska, and J. Wojaczyński Chem. Rev. 110 2010 4303 4356
25. A full electronic contribution has been observed when the sulfoxidation reaction was performed on methyl ester derivative 13, in which the electron withdrawing group at C-2 position made S-4 atom a weak nucleophile. However 13 could not be used for providing nucleoside 2, owing to fair instability of sulfoxide 14 to subsequent reaction conditions.
26. Theoretical calculations were performed by SPARTAN 08 Quantum mechanics program.
27. 2: C, 45.73, H, 4.43, N, 12.31, S, 18.78. Found: C, 45.80, H, 4.44, N, 12.28, S, 18.70.
28. 2: C, 42.01, H, 4.31, N, 16.33, S, 24.92. Found: C, 41.90, H, 4.32, N, 16.37, S, 24.99.
29. L.H.S. Smith, S.C. Coote, H.F. Sneddon, and D.J. Procter Angew. Chem., Int. Ed. 49 2010 5832 5844