Herein is described the synthesis of surfactants featuring polyhydroxylated head groups. Three head groups were prepared via consecutive stereoselective dihydroxylations of a diene. By coupling of these with lipophilic tail groups six novel surfactants have been prepared. The monolayers prepared from four of these have been investigated at the air-water interface. Significant differences were observed between monolayers consisting of enantiomerically pure surfactants contra racemates as well as between diastereomers.