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.
J. Yoshida, M. Nakagawa, H. Seki and T. Hino, J. Chem. Soc., Perkin Trans. 1, 1992, 343 DOI: 10.1039/P19920000343
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