A series of 2′, 3′-dideoxynucleosides based on the apiose family was prepared from photochemical ring-expansion of a common cyclobutanone precursor. The starting ketone,(±) 3-[2′-(benzoyloxy) ethyl]-2, 2-dimethylcyclobutanone (12) was prepared from commercially available (±) α-pinene. Since the optically pure antipodes of α-pinene are also commercially available, these nucleosides can be prepared optically pure using the ...
