A Chiral Building Block for the Stereocontrolled Installation of the 1,3-Diol Motif

A new chiral building block for the direct installation of the 1,3-diol motif is presented. Aldehyde olefination followed by directed reduction allows for the synthesis of both the syn- and the anti-configured diol in a fully stereocontrolled way. The building block was used for the total synthesis of naturally occurring 1,2,4-trihydroxynonadecanes starting from pentadecanal.