Chemoenzymatic synthesis of carbocyclic nucleoside analogues with bicyclo[3.1.0]hexyl residues

Abstract

The carbocyclic nucleoside analogues 8 and ent-8 have been prepared based on the enantiomerically pure bicyclo[3.1.0]hexane monoacetates 5 and ent-5 which were obtained by a lipase-catalysed asymmetrization of the meso-bicyclo [3.1.0] hexane derivatives 4 and 6, respectively. By an enantiodivergent approach both nucleoside analogues 8 and ent-8 have been synthesized starting from the common enantiomer 5. Furthermore, the adenine derivative ent-8 has been obtained from the monoacetate ent-5.