Highly Stereocontrolled and Regiocontrolled Syntheses of 2,3,4-Trisubstituted Alkanoates and Lactones

New chlorodiols (±)-3 and (±)-5 are densely functionalized and versatile synthons. They are converted in one step on a gram scale into 2-chlorolactones (±)-6 and (±)-7 and into 4-hydroxy glycidate esters (±)-9 and (±)-10. The 4-hydroxy glycidate esters (±)-9 and (±)-10 are converted stereospecifically and regiospecifically into oxazolines (±)-13 and (±)-14 and into cyclic carbamates (±)-18–(±)-20. The 4-hydroxy glycidate ester (±)-10 undergoes stereocontrolled and regiocontrolled epoxide opening by sodium azide to form the 2-azido-3,4-dihydroxy alkanoate (±)-21. Finally, chlorodiol (±)-5 reacts stereospecifically with silver triflate to form the 2,3-dihydroxyfuranone (±)-26.