An approach to the synthesis of cyclopentane analogues of the lyxosyl C-nucleosides

Abstract

The Diels–Alder adduct of cyclopentadiene and maleic anhydride has been converted into 5-endo,6-endo-O-isopropylidene-3-methoxycarbonylnorborn-2-ene. Cleavage of the double bond in this unsaturated ester affords methyl 2-(2′β,3′β-O-isopropylidene-4′β-methoxycarbonylcyclopent-1′β-yl)glyoxalate in which all the substituents are on the same side of the cyclopentane ring. This cyclopentane derivative is a potential synthon for cyclopentane analogues of the lyxosyl C-nucleosides, and its transformation into 5-(4′β-hydroxymethyl-2′β,3′β-dihydroxycyclopent-1′β-yl)-6-azauracil has been examined.