Synthesis of new ceramide analogues with allene in the sphingoid backbone

Ceramide is an important sphingolipid which can mediate a diverse range of biological activities. New ceramide analogues with an allene group in the sphingoid backbone were synthesized. The synthesis of the key intermediates involved the LiAlH(4)reduction of oxazolidine intermediates via a directed reduction-elimination reaction. Hydrolysis of the oxazolidine, liberation of the amino group, andN-acylation provided new ceramide analogues. These new analogues may provide new resources to study their bioactivities and the structure-activity relationship.