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Synthesis 2007(6): 929-935
DOI: 10.1055/s-2007-965935
DOI: 10.1055/s-2007-965935
PAPER
© Georg Thieme Verlag Stuttgart · New York
A General Route to 4-C-Substituted Pyrimidine Nucleosides
Further Information
Received
2 November 2006
Publication Date:
13 February 2007 (online)
Publication History
Publication Date:
13 February 2007 (online)
Abstract
Palladium-catalyzed cross-coupling reactions of tin and zinc nucleophiles with arylsulfonates of pyrimidine nucleosides have been achieved to give a wide range of 4-C-substituted pyrimidine nucleosides. This method also allows the construction of pyrimidine-pyrimidinone dinucleosides, containing the carbon skeleton of the (6-4) DNA photo lesion.
Key words
cross-coupling - nucleosides - palladium - pyrimidines - (6-4) lesion
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Galmarini CM.Jordheim L.Dumontet C. Exp. Rev. Anticancer Therapy 2003, 3: 717 - 2
Jeong LS.Lee JA. Antiviral Chem. Chemother. 2004, 15: 235 - 3
Gao K.Orgel LE. Nucleosides, Nucleotides Nucleic Acids 2000, 19: 935 - 4
Berber H.Soufyane M.Mirand C.Schmidt S.Aubertin AM. Tetrahedron 2001, 57: 7369 - 5
Friedel MG.Cichon MK.Carell T. In CRC Handbook of Organic Photochemistry and Photobiology 2nd ed.:Horspool WM. CRC Press; Boca Raton: 2004. p.141/1 - 6
Sekine M. J. Org. Chem. 1989, 54: 2321 - 7
Ding Y.Habib Q.Shaw SZ.Li DY.Abt JW.Hong Z.An H. J. Comb. Chem. 2003, 5: 851 - 8
Bischofberger N. Tetrahedron Lett. 1987, 28: 2821 - 9
Bischofberger N. Tetrahedron Lett. 1989, 30: 1621 - 10
Havelkova M.Dvorak D.Hocek M. Synthesis 2001, 1704 - 11
Capek P.Pohl R.Hocek M. Org. Biomol. Chem. 2006, 4: 2278 - 12
Hocek M.Naus P.Pohl R.Votruba I.Furman PA.Tharnish PM.Otto MJ. J. Med. Chem. 2005, 48: 5869 - 13
Lakshman MK.Thomson PF.Nuqui MA.Hilmer JH.Sevova N.Boggess B. Org. Lett. 2002, 4: 1479 - 14
Lakshman MK.Gunda P.Pradhan P. J. Org. Chem. 2005, 70: 10329 - 15
Acevedo OL.Andrews RS.Dunkel M.Cook PD.
J. Heterocycl. Chem. 1994, 31: 989 - 16
Switzer C.Shin D. Chem. Commun. 2005, 1342 - 17
Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508 - 18
Hayashi T.Konishi M.Kobori Y.Kumada M.Higuchi T.Hirotsu K. J. Am. Chem. Soc. 1984, 106: 158 - 19
Palmisano G.Santagostino M. Tetrahedron 1993, 49: 2533 - 20
Naus P.Votruba I.Hocek M. Collect. Czech. Chem. Commun. 2004, 69: 1955 - 21
Kunieda T.Witkop B. J. Am. Chem. Soc. 1971, 93: 3478 - 22
Coleman RS.Kesicki EA. J. Am. Chem. Soc. 1994, 116: 11636 - 23
Adamczyk M.Akireddy SR.Mattingly PG.Reddy RE. Tetrahedron 2003, 59: 5749 - 24
Bew SP.Sweeney JB. Synlett 1991, 109