Efficient Synthesis of a Styryl Analogue of (2S,3R,4E)‐N2‐Octadecanoyl‐4‐tetradecasphingenine via Cross‐Metathesis Reaction

Abstract

AbstractThe first total synthesis of sphingolipid (2S,3R,4E)‐N2‐octadecanoyl‐4‐tetradecasphingenine (1a), a natural sphingolipid isolated from Bombycis Corpus 101A, and of its styryl analogue 1b was achieved in good overall yield (Schemes 1 and 2). The key step involved the installation with (E) stereoselectivity of a long lipophilic chain or phenyl group on allyl alcohol derivative 3 via a cross‐metathesis reaction (→5a or 5b). The N‐Boc protected 3 was easily accessible from (S)‐Garner aldehyde.