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Synthesis of the butterfly compound (E,E)-10-hydroxy-3,7-dimethyldeca-2,6-dienoic acid
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1978
Year
EngineeringNatural SciencesDiversity-oriented SynthesisLithium Dimethylcuprate AdditionOrganic ChemistryButterfly CompoundChemistryTitle CompoundStereoselective SynthesisPharmacologyEnol PhosphateSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
The title compound was synthesized by alkylation of the dianion of methyl acetoacetate, and lithium dimethylcuprate addition to the enol phosphate of the alkylated β-keto esters (2) and (6) to produce the tri-substituted αβ-unsaturated esters (4) and (7) in a stereoselective manner.