Asymmetric total syntheses of spisulosine, its diastereo- and regio-isomers

Starting from palmityl alcohol divergent stereoselective syntheses of spisulosine and its diastereo- and regio-isomers have been achieved In the Sharpless asymmetric dihydroxylation-based approach the key step is the synthesis of monoprotected diol whereas Miyashita s boron-directed C-2 regioselective azidolysis of enantiomerically pure epoxy alcohol is the vital step in the Sharpless asymmetric epoxidation-based route The latter approach Involves the first protecting-group-free synthesis of spisulosine (C) 2010 Published by Elsevier Ltd