Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine.
The synthesis of naturally occurring D-erythro-(2R,3S,4E)-sphingosine from commercially available D-ribo-(2S,3S,4R)-phytosphingosine is described. The key step in the reaction sequence comprises TMSI/DBN promoted regio- and stereoselective oxirane opening of intermediate 2-phenyl-4-(S)-[(1S,2S)-1,2-epoxyhexadecyl]-1,3-oxazoline followed by the in situ trans-elimination of 2-phenyl-4-(S)-[(1S,2R)-1,2-dideoxy-2-iodo-1-trimethylsilyloxyhexadecyl]-1,3-oxazoline.
van den Berg
Richard J B H N
RJ
Cosmoferm B.V., P.O. Box 386, 2600 AJ Delft, The Netherlands.
Korevaar
Cornelius G N
CG
Overkleeft
Herman S
HS
van der Marel
Gijsbert A
GA
van Boom
Jacques H
JH
D001921:Brain; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; C481931:erythro-(2R,3S)-sphingosine; C012491:phytosphingosine; D013110:Sphingosine