A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach.
Starting from a vinylepoxide, a short and practical synthesis of D-erythro-sphingosine is described. The key transformations are a regioselective opening of the vinylepoxide and an E-selective cross-metathesis, affording the target molecule 5 in steps and 51% overall yield.
Torssell
Staffan
S
Organic Chemistry, KTH Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden.
Somfai
Peter
P
D002384:Catalysis; D015394:Molecular Structure; D013110:Sphingosine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D014753:Vinyl Compounds; D013110:Sphingosine