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Chiral and Stereoselective Total Synthesis of (−)-Deoxoprosopinine and (−)-Deoxoprosophylline. Intramolecular Amino mercuration of an ε,ζ-Unsaturated Amine
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References
1981
Year
Abstract L-serineBioorganic ChemistryEngineeringBiochemistryStereoselective Total SynthesisNatural SciencesChiral εOrganic ChemistryIntramolecular Amino MercurationStereoselective SynthesisChemistryζ-Unsaturated AmineChemical BiologyAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
Abstract l-Serine was transformed in 8 steps into (4R,5S)-2,2-dimethyl-4-[(Z)-3-pentadecenyl]-1,3-dioxan-5-amine. This chiral ε,ζ-unsaturated amine was subjected to intramolecular aminomercuration and then acid hydrolysis to give (−)-deoxoprosopinine and (−)-deoxoprosophylline.
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