Photochemical synthesis of novel dideoxynucleosides.
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 (+/-)alpha-pinene. Since the optically pure antipodes of alpha-pinene are also commercially available, these nucleosides can be prepared optically pure using the identical procedure.
Lee-Ruff
E
E
Department of Chemistry, York University, Toronto, Ontario, Canada.
Margau
R
R
D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010777:Photochemistry
D019380:Anti-HIV Agents; D015224:Dideoxynucleosides