Palladium-Catalyzed Alkynylation (Sonogashira Coupling) at C-5 of the Uracil Moiety in Modified Unsaturated Pyranosyl Nucleosides

Francisco J. B. Mendonça; Janaína V. dos Anjos; Denis Sinou; Sebastiao J. de Melo; Rajendra M. Srivastava

doi:10.1055/s-2007-965976

PSP

Palladium-Catalyzed Alkynylation (Sonogashira Coupling) at C-5 of the Uracil Moiety in Modified Unsaturated Pyranosyl Nucleosides

Jr. Francisco J. B. Mendonça^a,b, Janaína V. dos Anjos^a,c, Denis Sinou*^a, Sebastiao J. de Melo^b, Rajendra M. Srivastava*^c
^a Laboratoire de Synthèse Asymétrique, UMR 5246-ICBMS, ESCPE Lyon, Université Claude Bernard Lyon 1, 43 boulevard du 11 Novembre 1918, 69622 Villeurbanne Cedex, France
Fax: 33(4)78898914; e-Mail: sinou@univ-lyon1.fr;
^b Departamento de Antibióticos, Universidade Federal de Pernambuco, Cidade Universitária, 50670-901, Recife, PE, Brazil
^c Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, 50740-540, Recife, PE, Brazil
Fax: 55 8121268440; e-Mail: rms@ufpe.br;

Abstract

All articles of this category

Abstract

Various unsaturated 4-(5-substituted-uracil-1-yl)glycopyranosides were synthesized in good yields by a palladium-catalyzed cross-coupling reaction of ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-[5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]-α-d-erythro-hex-2-enopyranoside with a range of acetylenic derivatives.

Key words

palladium - unsaturated carbohydrates - cross-coupling - nucleoside

Full Text

References

1a De Clercq E. Med. Res. Rev. 1993, 13: 229

1b De Clercq E. Nucleosides Nucleotides 1994, 13: 1271

1c De Clercq E. J. Med. Chem. 1995, 38: 2491

1d Mansour TS. Storer R. Current Pharm. Design 1997, 3: 227

1e De Clercq E. Descamps J. Balzarini J. Giziewicz J. Barr PJ. Robins MJ. J. Med. Chem. 1983, 26: 661

1f Awano H. Shuto S. Baba M. Kira T. Shigeta S. Matsuda A. Bioorg. Med. Chem. Lett. 1994, 4: 367

1g Guenther S. Nair V. Nucleosides, Nucleotides Nucleic Acids 2004, 23: 183

2 Len C. Postel D. Curr. Org. Synth. 2006, 3: 261

3 Len C. Mackenzie G. Tetrahedron 2006, 62: 9085

4a Bowles WA. Robins RK. J. Am. Chem. Soc. 1964, 86: 1252

4b Kondo T. Nakai H. Goto T. Tetrahedron 1973, 29: 1801

4c Bolitt V. Chaguir B. Sinou D. Tetrahedron Lett. 1992, 33: 2481

4d Björsne M. Classon B. Kvarnström L. Samuelsson B. Tetrahedron 1993, 49: 8637

4e Pérez-Pérez MJ. Doboszewski B. Rozenski J. Herdewijn P. Tetrahedron: Asymmetry 1995, 6: 973

4f Polak M. Doboszewski B. Herdewijn P. Plavec J. J. Am. Chem. Soc. 1997, 119: 9782

4g Lee K. Zhou W. Kelley L.-LC. Momany C. Chu CK. Tetrahedron: Asymmetry 2002, 13: 1589

4h Procopio A. Dalpozzo R. De Nino A. Nardi M. Oliverio M. Russo B. Synthesis 2006, 2608

5a Konkel MJ. Vince R. Tetrahedron 1996, 52: 799

5b Rosenquist Å. Kvarnström I. Classon B. Samuelsson B. J. Org. Chem. 1996, 61: 6282

5c Wang J. Herdewijn P. J. Org. Chem. 1999, 64: 7820

5d Guan H.-P. Ksebati MB. Kern ER. Zemlicka J. J. Org. Chem. 2000, 65: 5177

6 de Oliveira RN. Mendonça FJB. Sinou D. de Melo SJ. Srivastava RM. Synlett 2006, 3049

7 Agrofoglio LA. Gillaizeau I. Saito Y. Chem. Rev. 2003, 103: 1875

8a Robins MJ. Barr PJ. Tetrahedron Lett. 1981, 22: 421

8b Robins MJ. Barr PJ. J. Org. Chem. 1983, 48: 1854

8c Robins MJ. Vinayah RS. Wood SG. Tetrahedron Lett. 1990, 31: 3731

8d McGuigan C. Yarnold CJ. Jones G. Velázquez S. Barucki H. Brancale A. Andrei G. Snoeck R. De Clercq E. Balzarini J. J. Med. Chem. 1999, 42: 4479

8e Kumarasinghe ES. Peterson MA. Robins MJ. Tetrahedron Lett. 2000, 41: 8741

8f Janeba Z. Maklad N. Robins MJ. Nucleosides, Nucleotides Nucleic Acids 2005, 24: 1729

8g Janeba Z. Balzarini J. Andrei G. Snoeck R. De Clercq E. Robins MJ. J. Med. Chem. 2005, 48: 4690

8h Janeba Z. Balzarini J. Andrei G. Snoeck R. De Clercq E. Robins MJ. Can. J. Chem. 2006, 84: 580

8i Crisp GT. Flynn BL. J. Org. Chem. 1993, 58: 6614

9 Cooke JWB. Bright R. Coleman MJ. Jenkins KP. Org. Process Res. Dev. 2001, 5: 383

10a Tornoe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057

10b Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

10c Bock VD. Hiemstra H. van Maarseveen JH. Eur. J. Org. Chem. 2006, 51

10d Wang Q. Chittaboina S. Barnhill HN. Lett. Org. Chem. 2005, 2: 293

11 de Oliveira RN. Cottier L. Sinou D. Srivastava RM. Tetrahedron 2005, 61: 8271

12 Rochet P. Vatele JM. Goré J. Synlett 1993, 105

13 Lindsell WE. Preston PN. Rettie AB. Carbohydr. Res. 1994, 254: 311

14 Marco-Contelles J. Ruiz-Caro J. Carbohydr. Res. 2001, 335: 71