Synthesis of 2amp;#x2032;-fluoro-6amp;#x2032;-methylene-carbocyclic adenosine (FMCA) and 2amp;#x2032;-fluoro-6amp;#x2032;-methylene-carbocyclic guanosine (FMCG)

摘要

The invention provides a new convergent approach for the synthesis of 2′-fluoro-6′-methylene-carbocyclic adenosine (FMCA) and 2′-fluoro-6′-methylene-carbocyclic guanosine (FMCG) from a readily available starting material in eight steps. An efficient and practical methodology for stereospecific preparation of a versatile carbocyclic key intermediate, (1S,3R,4R)-3-tert-butoxy-4-(tert-butoxymethyl)-2-fluoro-5-methylenecyclopentanol (compound 8 of scheme 1A or a) in only six (6) steps is also provided. Prodrugs of these compounds are also prepared.