Chiral carbocylic nucleosides: The synthesis and antiviral activity of 4′-hydroxy and 4′-fluorocarbocyclic - 2′- deoxyguanosines

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Abstract

The chiral carbocyclic nucleosides 2 and 3 were prepared from aristeromycin. The 4′α-hydroxy compound 2 displays good antiviral activity against HSV-1 and HSV-2 with low toxicity.

The chiral carbocyclic nucleosides 2 and 3 where prepared from aristeromycin. The 4′α-hydroxy compound 2 displays good antiviral activity against HSV-1 and HSV-2 with low toxicity.

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    Exposure of the compound (±)-371 to DAST, via an inversion of configuration and in 35% yield, gave the compound (±)-372, which was deprotected via acidic treatment to deliver the free nucleoside (±)-373. After Borthwick et al. accomplished the synthesis of the 4′-fluorocarbocyclic-2′-deoxyguanosine commencing with the commercially available aristeromycin (carbocyclic adenosine) in over 10 steps and showed that this nucleoside possessed good activities against HSV-1 and HSV-2,190 the Samuelsson group completed the synthesis of its analogue, 4′-fluorocarbocyclic-2′,3′-dideoxy-3′α-hydroxymethylguanosine 379, in 1999.191 In their synthesis (Scheme 67), the cyclopentanol 378 was prepared from the enantiomerically pure (3S,4S)-bis(hydroxylmethyl)cyclopentanone ethylene glycol ketal 374 in 10 steps involving stereospecific reduction of the keto function of compound 375 and dihydroxylation of the C-4 methylene of 376.

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