131606-87-6Relevant academic research and scientific papers
Total synthesis of symbioramide: A flexible approach for the efficient preparation of structural isomers
Prevost, Sebastien,Ayad, Tahar,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie
, p. 3213 - 3226 (2011)
A concise, enantioselective total synthesis of symbioramide, starting from simple achiral compounds and racemic α-amino-β-keto ester derivatives is reported. This highly flexible strategy allowed the efficient preparation of seven structural isomers of the natural product as well. The synthesis relies on a convergent route that involves the efficient stereoselective reduction of a α-keto-β-yne ester, and the dynamic kinetic resolution of an α-amino-β-keto ester through ruthenium-mediated asymmetric hydrogenation. Copyright
Total Synthesis of Symbioramide, a Novel Ca(2+)-ATPase Activator from Symbiodinium sp.
Yoshida, Jun,Nakagawa, Masako,Seki, Hiroko,Hino, Tohru
, p. 343 - 350 (2007/10/02)
The first total synthesis of symbioramide 1 has been accomplished by the coupling of D-erythro-dihydrosphingosine with an unusual, chiral α-hydroxy-β,γ-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.
First Total Synthesis of Symbioramide, a Novel Ca2+-ATPase Activator from Symbiodinium sp.
Nakagawa, Masako,Yoshida, Jun,Hino, Tohru
, p. 1407 - 1410 (2007/10/02)
The first total synthesis of symbioramide (1) is described and simultaneously established the complete stereostructure of 1 to be (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine.
