The synthesis of a series of different fluorinated analogues
of sphinganine and dihydroceramide using Staudinger ligation of
diastereomeric 2-azido-4-fluoro-3-hydroxyoctadecanoates and subsequent
selective ester reduction as key steps is presented. The formed
sphingolipid analogues are interesting for medicinal studies as
well as for the investigation of their phase behavior at interfaces.
sphingolipids - asymmetric synthesis - acylation - fluorination - amides
