Highly stereocontrolled access to a tetrahydroxy long chain base using anti-selective additions

Article abstract of DOI:10.1039/a902386k

Complete diastereostereoselection was attained for the addition of acetylide and benzyloxymethyl anions to a chiral aldehyde and an imine derived from meso-tartaric acid, leading to a facile synthesis of (2S,3S,4R,5R,6Z)-2-amino-1,3,4,5-tetrahydroxyoctadecene as its pentaacetyl derivative in enantiomerically pure form.