Enantioselective Synthesis and Conformational Analysis of Cyclohexene Carbocyclic Nucleosides |
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| Authors: | Jing Wang Piet Herdewijn |
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| Institution: | Laboratory of Medicinal Chemistry , Rega Institute for Medical Research, K. U. Leuven , Minderbroedersstraat 10, B-3000, Leuven, Belgium |
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| Abstract: | Abstract An enantioselective approach towards the synthesis of optically pure cyclohexene nucleosides 3 has been developed starting from (R)-carvone. The key steps are the regio- and stereoselective hydroboration of an exo double bond, the selective reduction of an enone intermediate and introduction of a base moiety by Mitsunobu reaction. Conformational analysis showed that the adenine base adopts predominantly in a pseudo-axial position. |
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