Aspects of the chemistry of dioxolanes: Synthesis of C-nucleoside analogues

Article abstract of DOI:10.1016/S0040-4020(97)10274-5

Chiral 2-formyl and 2-(1-oxoalkyl)-1,3-dioxolanes have been prepared by ozonolysis of the corresponding alkenes and by oxidation of 2-(1-hydroxyalkyl)-1,3-dioxolanes, which are readily available from 2-(tributylstannyl)dioxolanes, and taken through to αβ-unsaturated esters by condensation with stabilized ylids. The (4'S,5'S)-1-benzyl-5-[4,5-bis(ethoxycarbonyl)-1,3-dioxolan-2-yl]-2-pyridone 47 was prepared as an anologue of a C-nucleoside, but was found to be unstable.