Practical Synthesis of d- and l-2-Cyclopentenone and Their Utility for the Synthesis of Carbocyclic Antiviral Nucleosides against Orthopox Viruses (Smallpox, Monkeypox, and Cowpox Virus)

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Abstract
Highly efficient and practical methodology for the syntheses of d- and l-4,5-O-isopropylidene-2-cyclopentenone (9 and 22), versatile intermediates for the synthesis of carbocyclic nucleosides, have been developed via a ring-closing metathesis reaction from d-ribose in eight steps. The utility of d- and l-4,5-O-isopropylidene-2-cyclopentenone is demonstrated by their application for the preparation of d-cyclopentyl-6-azauridine 12 and d-cyclopentenyl-5-halocytosine nucleosides (33−35) using Mitsunobu reaction to introduce pyrimidine bases as potential antiviral agents. Preliminary antiviral activity against orthopox viruses (smallpox, monkeypox, and cowpox virus) of the synthesized nucleosides are described.