Synthesis of potential inhibitors of the glycosphingolipid biosynthesis

Article abstract of DOI:10.1016/S0040-4020(01)90177-2

A synthesis of ceramide analogs 6 and 7 is reported here starting from L-cysteine. Alkylation of 2 and subsequent reduction of the intermediate formed ketone 3 afforded the diastereomeric alcohols 4. Deprotection and acylation of 4 lead to the desired product 6 which is converted to the sulfonium salt 7. Compound 6 is a powerful inhibitor of the glycosphingolipid biosynthesis.