A direct organocatalytic entry to sphingoids: asymmetric synthesis of D-arabino- and L-ribo-phytosphingosine.
The organocatalytic asymmetric synthesis of D-arabino- and L-ribo-phytosphingosine is described employing a diastereo- and enantioselective (S)-proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxan-5-one and pentadecanal as the key step.
Enders
Dieter
D
Institut für Organische Chemie, RWTH Aachen, Landoltveg 1, 52074 Aachen, Germany. enders@rwth-aachen.de
Palecek
Jirí
J
Grondal
Christoph
C
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D004146:Dioxanes / Q000737:chemistry; D008956:Models, Chemical; D011392:Proline / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; C519228:D-arabino-phytosphingosine; D004146:Dioxanes; C519227:L-ribo-phytosphingosine; C003061:pentadecanal; D011392:Proline; D013110:Sphingosine