Synthesis of carbocyclic analogues of 1-beta-D-psicofuranosyl nucleosides: psico-cyclopentenyladenosine (psicoplanocin A) and psico-Cyclopentenylcytosine

Carbocyclic ketohexose nucleosides is represented by psicoplanocin A and psico-cyclopenetenyladenosine. Geometrical characteristics of neplanocin A and the ketohexose nucleosides psicofuranine and decoynine are fused in the two steady compounds. Cyclopentenone is used to prepare both compounds in racemic form. D-ribonolactone yields the cyclopentenone required for the synthesis. An insulated hydroxymethyl segment is linked to the ketone carboxyl of the cyclopentenone to initiate the creation of surrogate glycon moiety, through nucleophilic incorporation of ((benzoyloxy)methyl)lithium to produce an intermediate.