An Efficient Synthesis of Phosphonate Derivatives of 1,2-Disubstituted Carbocyclic Purine Nucleosides with a Cyclopentane Ring

Abstract

The synthesis of phosphonate 1,2-disubstituted carbocyclic nucleosides with a cyclopentane ring is described following two different strategies: inclusion of the phosphonomethyl group before or after coupling of the carbocyclic moiety with the heterocyclic base. The diethyl [(trifluoromethanesulfonyl)oxy]methanephosphonate is the key phosphonylating agent for both the strategies.

Key words

nucleosides - phosphonates - carbocycles - Mitsunobu reaction

References

• 1a Chu CK. Recent Advances in Nucleosides: Chemistry and Chemotherapy   Elsevier; Amsterdam: 2002. 
• 1b Simons C. Nucleoside Mimetics: Their Chemistry and Biological Properties   Gordon and Breach Science Publishers; Amsterdam: 2001. 
• 1c De Clercq E. J. Clin. Virol.  2004,  30:  115 
• 1d Johnson SA. Expert Opin. Pharmacother.  2001,  2:  929 
• 2a Kukhanova M. Krayevsky A. Prusoff W. Cheng YC. Curr. Pharm. Des.  2000,  6:  585 
• 2b El Kouni MH. Curr. Pharm. Des.  2002,  8:  581 
• 2c Poijärvi-Virta P. Lönnberg H. Curr. Med. Chem.  2006,  13:  3441 
• 3 Holý A. Advances in Antiviral Drug Design   JAI; Greenwich: 1993. 
• 4 De Clercq E. Holý A. Nat. Rev. Drug Discov.  2005,  4:  928 
• 5a Kim CU. Luh BY. Martin JC. J. Org. Chem.  1991,  56:  2642 
• 5b Kim CU. Luh BY. Misco PF. Martin JC. Nucleosides Nucleotides  1991,  10:  371 
• 6 Jähne G. Müller A. Kroha H. Rösner M. Holzhäuser O. Meichsner C. Helsberg M. Winkler I. Riess G. Tetrahedron Lett.  1992,  33:  5335 
• 7a Santana L. Teijeira M. Terán M. Uriarte E. Viña D. Synthesis  2001,  1532 
• 7b Besada P. González-Moa MJ. Terán C. Santana L. Uriarte E. Synthesis  2002,  2445 
• 7c Viña D. Santana L. Uriarte E. Terán C. Tetrahedron  2005,  61:  473 
• 8 Estrada E. Uriarte E. Montero A. Teijeira M. Santana L. De Clercq E. J. Med. Chem.  2000,  43:  1975 
• 9 Santana L. Teijeira M. Uriarte E. Balzarini J. De Clercq E. Bioorg. Med. Chem. Lett.  1998,  8:  1349 
• 10 Holý A. Rosenberg I. Collect. Czech. Chem. Commun.  1982,  47:  3447 
• 11 Jeffery AL. Kim J.-H. Wiemer DF. Tetrahedron  2000,  56:  5077 
• 12 Esteban-Gamboa A. Balzarini J. Esnouf R. De Clercq E. Camarasa MJ. Pérez-Pérez MJ. J. Med. Chem.  2000,  43:  971 
• 13 Phillion DP. Andrew SS. Tetrahedron Lett.  1986,  27:  1477 
• 14 McKenna CE. Schmidhauser J. J. Chem. Soc., Chem. Commun.  1979,  739 
• 15 Kluge AF. Org. Synth.  1986,  64:  80