A concise synthesis of symbioramide, a marine-origin ceramide from a common starting material, methyl (±)- trans-2,3-epoxyoctadecanoate, in a convergent manner was achieved. The key step is the direct lipase-catalyzed coupling reaction between methyl (2 R,3 E)-2-hydroxy-3-octadecenoate and non-protected (±)- erythro-dihydrosphingosine, giving natural (2 S,3 R,2′ R)-symbioramide and its (2 R,3 S,2′ R)-isomer in 38% and 37% yield, respectively. The optically active β,γ-unsaturated α-hydroxyester was prepared by Mg(ClO 4) 2-mediated isomerization of epoxide and the subsequent lipase PS-catalyzed kinetic resolution.