A Simple Synthesis of all four Stereoisomers of 2,2,5-Trimethyl-1,3-dioxolane-4-carbaldehyde

Article abstract of DOI:10.1007/BF01277638

A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed.Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage.This procedure allows an application on a multigram scale. - Keywords. 2,2,5-Trimethyl-1,3-dioxolane-4-carbaldehydes, aldopentose diethyl dithioacetals, lead tetraacetate cleavage.