Chemoenzymatic synthesis of novel adenosine carbanucleoside analogues containing a locked 3′-methyl-2′,3′-β-oxirane-fused system |
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Authors: | Yoann Aubin Nicolas Vanthuyne |
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Affiliation: | a Laboratoire de Réactivité Organique Sélective, U.M.R. 6180 ‘Chirotechnologies: catalyse et biocatalyse’, Université Paul Cézanne—Aix-Marseille III, 13397 Marseille Cedex 20, France b Laboratoire de Stéréochimie Dynamique et Chiralité, U.M.R. 6180 ‘Chirotechnologies: catalyse et biocatalyse’, Université Paul Cézanne—Aix-Marseille III, 13397 Marseille Cedex 20, France |
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Abstract: | Starting from a readily available enantiopure building block, a straightforward enantioselective approach to 3′-methyl-2′,3′-β-oxirane-fused carbanucleosides bearing adenosine analogues is detailed. The key steps in the syntheses involved a lipase-catalyzed regioselective monoacylation of a diol to obtain the key intermediate and direct coupling of this key intermediate with diversely substituted purine nucleobases under Mitsunobu reaction conditions providing only the N9 target molecules. |
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Keywords: | Carbocyclic nucleosides Mitsunobu coupling reaction Stereocontrolled epoxidation Lipase regioselectivity |
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