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■ Synthesis of Nucleosides and Their Related Compounds. 15. Dimethyl rel-(1S,2S,3R,4R)-2-(2,3-Epoxy-4-hydroxymethylcyclopent-1-yl)Malonate as a Novel Building Block for Carbocyclic Arabinosyl Nucleosides

Nobuya Katagiri, Masahiro Nomura, and Chikara Kaneko

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Dimethyl 3-acetoxy-5,6-exo-epoxybicyclo[2.2.1]heptane-2,2-dicarboxylate (1) has been synthesized by epoxidation of the Diels-Alder adduct of dimethyl acetoxymethylenemalonate with cyclopentadiene and on reductive retrograde aldol reaction afforded dimethl rel-(1S,2S,3R,4R)-2-(2,3-epoxy-4-hydroxymethylcyclopent-1-yl)malonate (2), which serves as the direct precursor of carbocyclic arabinosyl nucleosides. Synthesis of the related bicyclo-epoxides and their reactions are also described.