Total synthesis of symbioramide, a novel Ca2+-ATPase activator from Symbiodinium sp

Abstract

The first total synthesis of symbioramide 1 has been accomplished by the coupling of D-erythro-dihydro-sphingosine with an unusual, chiral α-hydroxy-βγ-unsaturated fatty acid prepared from L-ascorbic acid, and simultaneously established the complete stereostructure of 1 to be (2S, 2′R, 3R, 3′E)-N-(2′-hydroxyoctadec-3′-enoyl)dihydrosphingosine.