Enantiodivergent synthesis of cyclohexenyl nucleosides.
An enantiodivergent synthesis of several cyclohexenyl nucleosides has been efficiently completed starting from the enantiopure hydrobenzoin-derived monoketal of cyclohex-2-en-1,4-dione, (+)-5. Stereodiversity was accomplished on the base coupling step. This methodology has proved to be useful for the synthesis of enantiopure pyrimidine and purine nucleoside analogues, which anti-HIV activity has been evaluated.
Ferrer
Eric
E
Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
Alibés
Ramon
R
Busqué
Félix
F
Figueredo
Marta
M
Font
Josep
J
de March
Pedro
P
D019380:Anti-HIV Agents; D001573:Benzoin; D053138:Cyclohexenes / Q000138:chemical synthesis*; D009705:Nucleosides / Q000138:chemical synthesis*; D011687:Purines / Q000138:chemical synthesis; D011743:Pyrimidines / Q000138:chemical synthesis
D019380:Anti-HIV Agents; D053138:Cyclohexenes; D009705:Nucleosides; D011687:Purines; D011743:Pyrimidines; D001573:Benzoin