title: Synthesis of D-erythro-sphinganine through serine-derived α-amino epoxides.
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.
authors.affiliation: Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Università della Calabria , Edificio Polifunzionale, I-87030 Arcavacata di Rende (CS), Italy.
authors.forename: Carlo
authors.initials: C
authors.lastname: Siciliano
authors.forename: Anna
authors.initials: A
authors.lastname: Barattucci
authors.forename: Paola
authors.initials: P
authors.lastname: Bonaccorsi
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Di Gioia
authors.forename: Antonella
authors.initials: A
authors.lastname: Leggio
authors.forename: Lucio
authors.initials: L
authors.lastname: Minuti
authors.forename: Emanuela
authors.initials: E
authors.lastname: Romio
authors.forename: Andrea
authors.initials: A
authors.lastname: Temperini
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D012694:Serine / Q000031:analogs & derivatives* / Q000737:chemistry; D013110:Sphingosine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; C000594716:N-tert-butyloxycarbonyl-L-serine methyl ester; D012694:Serine; C429009:serine methyl ester; D013110:Sphingosine