Desymmetrisation and ring opening of cyclohexa-1,4-dienes. An access to highly functionalised cyclic and acyclic systems

Acyclic and cyclic synthons are readily available in three steps starting from substituted arenes. Birch reduction of the latter followed by desymmetrisation through Sharpless AD reaction then ozonolysis thus afforded five-membered ring lactols and acyclic polyols with good to excellent stereocontrol in high yields.