A convergent total synthesis of a new antiepileptic ceramide and its triacetyl derivative using olefin cross metathesis

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 functionalized 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.