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A novel carbovir analog, (±)-2-amino-1,6-dihydro-6-oxo-9-(4-bis(hydroxymethyl)-2- cyclopenten-1-yl)-9H-purine, was synthesized starting from the γ-lactam, 2-azabicyclo (2.2.1)hept-5-en-3-one (7). The key intermediate, 1-acetamido-4-bis(hydroxymethyl)cyclopent- 2-ene (10), was prepared by the Pfitzner-Moffatt oxidation of the hydroxymethyl group of 8, aldol condensation of the resulting aldehyde, followed by a Cannizzaro reaction. The guanine base was constructed on the amino group of 10. The structures of the target molecule and the intermediates were confirmed by NMR, UV and HRMS data. Anti-HIV evaluation results are reported.

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Synthesis and antiviral evaluation of 2-amino-1,6-dihydro-6-oxo-9-[4-bis(hydroxymethyl) -2-cyclopenten-1-yl]-9H-purine: an analog of the anti-HIV compound Carbovir