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Chiral synthesis of (+)-eburnamine, (–)-eburnamenine, and (–)-eburnamonine
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1985
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Diversity Oriented SynthesisBioorganic ChemistryEngineeringBiochemistryNatural SciencesDiversity-oriented SynthesisL-glutamic AcidOrganic ChemistryStereoselective SynthesisPharmacologyChiral SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
The (S)-trityl-lactone (6), easily prepared from L-glutamic acid or D-mannitol, has been stereo-selectively converted into (+)-eburnamine (3), (–)-eburnamenine (4), and (–)-eburnamonine (2), via the dithiane-lactone (15).