The investigation of brand new compounds with potential anti-viral activity is currently in the limelight of worldwide research, in particular with regard to the will to eradicate the HIV virus. In this context, after the chemical synthesis approach, that has produced several drugs capable of slowing the course of the disease and improving the survival expectations, the latest research trends are involved in the search for anti-viral compounds from natural sources which could be active by themselves or may furnish their basic structures as useful building blocks to be employed in semisynthetic approaches. Our most recent research line is mainly focused on the latter aspect, i.e. the use of natural products as starting materials for the semisynthesis of antiviral derivatives. In this work we report a double synthetic scheme to obtain three potential precursors for the synthesis of nucleoside analogs with a carbocyclic skeleton starting from harpagide and its 8-O-acetylderivative which are well known enantiopure compounds of natural origin.