Stereoselective synthesis of (±)-ancistrofuran: stereoselective reduction of a γ-hydroxyketone

A remarkably stereoselective reduction of a γ-hydroxyketone with two equiv. of lithium triethylborohydride has been observed and this effect has been suggested to originate from ‘chelation control’; the reaction has been utilised in a short stereoselective synthesis of ancistrofuran.