Organic Letters · 2008 · 66 citations · 48 references
Natural SciencesBiochemistryChemistryOrganic ChemistryLipid BiosynthesisOrganic SynthesisRetrosynthetic AnalysisAllylic FunctionalizationAllylic SubstitutionChiral Intermediate ProductionChiral Product SynthesisEnantioselective Synthesis
A general and efficient protocol for the enantioselective synthesis of sphingosine, phythosphingosine, and 4-substituted derivatives was established. These compounds were obtained from a common intermediate prepared from butadiene monoepoxide by a synthetic sequence involving enantioselective allylic substitution, cross-metathesis, and dihydroxylation.
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