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Asymmetric synthesis of 3-methyl-2-phenyl-1,4-benzodioxanes. Absolute configuration of the neolignans eusiderin and eusiderin C and D
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1985
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Natural NeolignansEusiderin DAbsolute ConfigurationEngineeringHeterocyclicNatural SciencesDiversity-oriented SynthesisAsymmetric SynthesisOrganic ChemistryStereoselective SynthesisChemistryHeterocycle ChemistryPharmacologySynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
The asymmetric synthesis of 2S,3S- and 2R,3S-3-methyl-2-phenyl-1,4-benzodioxane from (–)-ephedrine is reported. Comparison of the c.d. curves of these compounds with those of the natural neolignans eusiderin and eusiderin C allows the assignment of 2R,3R configuration to eusiderin and of 2R,3S configuration to eusiderin C and eusiderin D.