Synthesis of (2S,3R,4E,8E)-9-methyl-4,8-sphingadienine via a novel S(N)2' type reaction mediated by a thioether carbanion

Article abstract of DOI:10.1016/S0040-4039(99)01885-7

A stereoselective synthesis of sphingadienine 3 as a new analogue of sphingosine has been achieved by a novel copper, catalyzed S(N)2' type homoallylic coupling reaction between an allylic mesylate and a thioether- stabilized allylic carbanion.