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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Synthesis of D-erythro-sphinganine through serine-derived α-amino epoxides
Carlo Siciliano1, Anna Barattucci, Paola Bonaccorsi
1Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Università della Calabria , Edificio Polifunzionale, I-87030 Arcavacata di Rende (CS), Italy.
Abstract:
A total synthesis of D-erythro-sphinganine [(2S,3R)-2-aminooctadecane-1,3-diol] starting from commercial N-tert-butyloxycarbonyl-L-serine methyl ester is described. The approach is based on the completely stereoselective preparation of an α-amino epoxide obtained by treating a protected L-serinal derivative with dimethylsulfoxonium methylide. The oxirane synthon is obtained with an anti configuration fitting the (2S,3R) stereochemistry of the 2-amino-1,3-diol polar head of D-erythro-sphinganine. The synthetic procedure afforded the target compound in a 68% overall yield based on the initial amount of the starting L-serine material.
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