Natural α-hydroxy acids have been converted in a sequence of O-protection, reduction, O- activation, thioether and ether formation and deprotection to chiral, non-racemic β, β′- dihydroxy thioethers 1a, 1b and ether 1c. Overall yields are excellent (75%). In an attempt to synthesize the respective dihydroxy ether 1d derived from mandelic acid 1, 3-dioxolane derivatives 7 were obtained.
