Stereocontrolled synthesis of 5-(1′-hydroxyalkyl)-3-methylidenetetrahydro-2-furanones

Diastereo- and enantioselective synthesis of 5-(1′-hydroxyalkyl)-3-methylidenetetrahydro-2-furanones from 2-diethoxyphosphoryl-4-alkenoic acids or 2-diethoxyphosphoryl-4-alkenoates was readily accomplished using novel methodology involving syn- or anti-dihydroxylation procedures combined with Horner–Wadsworth–Emmons olefination techniques.