Synthesis of trans-fused tetrahydropyrans via intramolecular cyclization of α-bromo-γ'-hydroxy ketones

Article abstract of DOI:10.1016/S0040-4039(99)01323-4

A practical method for the synthesis of trans-fused polytetrahydropyrans using racemic cis- and trans-epoxy sulfones was developed. Four diastereoisomers, obtained by the reaction of an optically active triflate and the oxiranyl anions generated from racemic cis- and trans-epoxy sulfones, were transformed into α-bromo-γ'-hydroxy ketones, and the DBU-induced intramolecular cyclization gave tetrahydropyranones.