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A very simple synthetic route of a novel SATE prodrug type of 6'-fluoro-6'-methyl-5'-noradeonosine carbocyclic nucleoside phosphonic acid is described. The key fluorinated alcohol intermediate 7 was prepared from the epoxide intermediate 6a via selective ring-opening of epoxide. Coupling of 7 with N 6 -bis-Boc-adenine under a Mitsunobu reaction followed by phosphonation and deprotection afforded the carbocyclic phosphonic acid. The chemical stability of the bis(SATE) derivative 13 was measured at neutral (pH 7.2) and slightly acidic (Milli-Q water, pH 5.5) pH. The antiviral activity test of the SATE prodrug 13 and its parent nucleoside phosphonic acid 11 were evaluated against HIV-1.

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Nucleic acids U 0700 Synthesis of 3'(β)-C-Methyl Carbodine Analogues as Potential anti-HCV Agents-The novel title compounds (IX) are prepared via a sigmatropic rearrangement and a metathesis reaction as key steps They do not show antiviral or toxic activity. -(LI, H.; BAIK, Y. C.; HONG*, J. H.; Bull. Korean Chem.

The synthetic route of novel 3′-C-methyl carbodine analogue is described. The construction of tertiary alcohol at 3′-position of carbodine analogues was successfully made via sequential [3,3]-sigmatropic rearrangement, ring-closing metathesis (RCM) and stereoselective dihydroxylation reactions starting from ethyl glycolate.