Abstract

The singlet oxygen oxygenation of 2-(α-C-glucopyranosyl)furans 1 leads readily and diastereoselectivity to the corresponding endoperoxides 2 whose fate can be controlled. Compounds 2 thermally rearrange into cis-dicarbonyl-α-O-glucosides 3 while by reduction they afford the cis-C-analogs 5. The latter readily convert to trans-8, which by silica gel chromatography tautomerize into β-anomers 9.

Keywords: photooxygenation, 2-(c-glucopyranosyl)furans, o-glucopyranosides, c-glucopyranosides, furan-based synthesis, cis-1,4-dioxo-2-alkenyl glucopyranosides