University of Georgia Research Foundation, Inc.

Anterogen Co. Ltd.

Uma Sharan Singh

Chung K Chu

Varughese Alexander Mulamootttil

Ram C Mishra

Varughese Alexander Mulamoottil

In an embodiment, the invention is directed to prodrug compounds of L-BHDU according to the chemical structure I:

Prodrugs of L-BHDU and methods of treating viral infections

The invention provides a new convergent approach for the synthesis of 2'-fluoro-6&#x2032;-methylene-carbocyclic adenosine (FMCA) and 2&#x2032;-fluoro-6&#x2032;-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.

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

The invention provides a new convergent approach for the synthesis of 2'-fluoro-6&#x2032;-methylene-carbocyclic adenosine (FMCA) and 2&#x2032;-fluoro-6&#x2032;-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.

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Athens, GA, United States of America

Uma Sharan Singh