A Convergent Total Synthesis of a New Antiepileptic Ceramide and its Triacetyl Derivative Using Olefin Cross Metathesis

Abstract

A convergent total synthesis of a new antiepileptic ceramide 1b and its triacetyl derivative 1b' was completed by using two important C-C bond forming reactions, Wittig methylenation and olefin cross metathesis as the key steps. The easily available 3, 4, 6-tri-O-benzyl-D-galactal was used as a chiral pool for the synthesis of highly functionalised amide 3 and the commercially available 1, 12-dodecanediol for the long chain olefin counterpart 4. The long hydrocarbon chain of the new ceramide 1b was installed by using olefin cross metathesis between amide 3 and long chain terminal olefin 4 followed by hydrogenation.