Synthesis of new ceramide analogues with allene in the sphingoid backbone

Abstract

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 LiAlH₄ reduction of oxazolidine intermediates via a directed reduction-elimination reaction. Hydrolysis of the oxazolidine, liberation of the amino group, and N-acylation provided new ceramide analogues. These new analogues may provide new resources to study their bioactivities and the structure-activity relationship.

Graphical Abstract

Keywords:

• Ceramide
• allene
• analogues
• synthesis
• directed reduction-elimination

Additional information

Funding

This work was supported by Foundation of Jiangxi Province Educational Committee (KJLD14079).