An efficient asymmetric synthesis of Enigmols (1-deoxy-5-hydroxysphingoid bases), an important class of bioactive lipid modulators.

An enantioselective synthesis of the four 2S-diastereomers of enigmol (2-amino-octadecane-3,5-diols) from L-alanine is reported. The procedure described is robust, highly stereoselective at each step, and suitable for preparation of gram quantities of material. [ABSTRACT FROM AUTHOR]