Stereocontrol in the addition of nucleophiles to an optically active aldehyde derived from L-serine, leading to a short-step synthesis of (2S,3S,4R)-phytosphingosine

Article abstract of DOI:10.1016/S0040-4039(97)01340-3

The diastereoselective addition of dithianide to a chiral aldehyde derived from L-serine followed by hydrolysis of the dithiane moiety and the addition of dodecylacetylide gave diastereomerically pure aminotriol derivative which, upon hydrogenation and deprotection, afforded (2S,3S,4R)-phytosphingosine in good overall yield in enantiomerically pure form.