Stereocontrolled synthesis of a sphingomyelin methylene analogue as a sphingomyelinase inhibitor

[GRAPHICS] Efficient synthesis of a sphingomyelin methylene analogue, which was design ed as a sphingomyelinase inhibitor, was stereoselectively achieved. The Hof mann rearrangement of the alpha-hydroxyethyl beta-hydroxy amide 4 followed by the intramolecular oxazolidinone ring formation was one of the key steps .