Abstract
Dye-sensitized photooxygenation of 2-methyl 5-(2,3,5-tri- O-acetyl-β- d-ribofuranosyl)furoate leads to (1 S,4 R)- endo-peroxide, highlighting a high facial diastereoselectivity. This endo-peroxide rearranges into syn-(1 R,2 R:3 S,4 R)-diepoxide C-nucleoside, while by Et 2S-reduction followed by NEt 3 catalysis affords a spirocyclic C-nucleoside.
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