An efficient synthesis of D-ribo- and L-lyxo-phytosphingosine from D-tartaric acid

Article abstract of DOI:10.1016/j.tetlet.2005.03.063

The preparations of D-ribo- and L-lyxo-phytosphingosines (1, 2) are described. Chelation-controlled addition of tetradecylmagnesium bromide to pentylidene-protected D-threitol aldehyde 6 afforded the key intermediate tetrol 7, providing the desired L-lyxo stereochemistry of phytosphingosine. Inversion at C4 of intermediate 7 provided the D-ribo stereochemistry.