Synthesis of novel Bi-, Tri-, and tetracyclic nucleosides by reaction of a common cyclic enamine derived from TSAO-T with nucleophiles.
We report here the efficient regio- and stereoselective synthesis of new polycyclic nucleosides using a common cyclic enamine (7) as the starting material. In fact, the reaction of 7, easily prepared by reaction of 5'-O-Tosyl TSAO-T under basic nonnucleophilic conditions (potassium carbonate), with different classes of nucleophiles, for example, nitrogen-, oxygen-, sulfur-, and carbon-based nucleophiles, or with amino acids afforded, with total regio- and stereoselectivity, new bi-, tri-, and tetracyclic nucleosides. This straighforward route represents an original and unambiguously regio- and stereoselective pathway to these compounds. Some of these polycyclic nucleosides may be useful intermediates for a second series of reactions that may lead to the generation of structurally new nucleosides.
Bonache
María-Cruz
MC
Instituto de Química Médica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.
Chamorro
Cristina
C
Cordeiro
Alessandra
A
Camarasa
María-José
MJ
Jimeno
María-Luisa
ML
San-Félix
Ana
A
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives
D000588:Amines; D019380:Anti-HIV Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D009705:Nucleosides; D013141:Spiro Compounds; D013936:Thymidine; C075132:TSAO-T; D014529:Uridine