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| - Enantioselective Synthesis and Conformational Study ofCyclohexene Carbocyclic Nucleosides
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| - Enantioselective synthesis of a new family of unsaturated six-membered carbocyclic nucleosidesusing (R)-(−)-carvone as starting material is described. Introduction of the base moiety viaMitsunobu reaction proceeded regio- and stereoselectively and with good chemical yield, while thePd-coupling approach failed. 1H NMR study and molecular modeling show the adenine compoundexists in an equilibrium of 3H2 and 2H3 conformers (ratio 7:3) in favor of the 3‘-endo half-chairconformation, with the base oriented in a pseudoaxial position. This conformational preferencecan be explained by the π → σ*C1‘-N1 interaction involving the antibonding orbital of the C1‘−Nbond.
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