Divergent synthesis of D-erythro-sphingosine, L-threo-sphingosine, and their regioisomers.
Starting from a vinyl epoxide, a divergent synthesis of four sphingosine isomers is described. The remaining four isomers can easily be synthesized using the same methodology. Although numerous syntheses of sphingosine have been published, this is the first general route leading to all eight isomers in this important compound class. The synthetic strategy relies on regioselective opening of a vinyl epoxide and a vinylaziridine in the allylic position.
Olofsson
Berit
B
Department of Chemistry, Organic Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden.
Somfai
Peter
P
D001388:Aziridines / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007202:Indicators and Reagents; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D001388:Aziridines; D007202:Indicators and Reagents; D014753:Vinyl Compounds; D013110:Sphingosine