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Chirospecific Synthesis of (<i>S</i>)-(+)- and (<i>R</i>)-(-)-5-Amino-4-hydroxypentanoic Acid from L- and D-Glutamic Acid via (<i>S</i>)-(+)- and (<i>R</i>)-(-)-5-Hydroxy-2-oxopiperidine
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1986
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Pharmaceutical ScienceD-glutamic AcidBioorganic ChemistryOrganic ChemistryPharmaceutical ChemistryMedicinal ChemistryBiosynthesisDiversity Oriented SynthesisStereoselective SynthesisFive-step SequenceBiochemistryInteresting Acid GabobDiversity-oriented SynthesisDrug DevelopmentPharmacologyNatural Product SynthesisBiomolecular EngineeringNatural SciencesChirospecific SynthesisMedicineSynthetic ChemistryDrug Discovery
5-Hydroxy-2-oxopiperidine, which we earlier prepared from 5-hydroxy-2-pyridene can now be prepared stereospecifically [(S)-(+)- and (R)-(-)isomers] from L- and D-glutamic acid, respectively, by a five-step sequence. Ring cleavage of (S)-(-)-5-hydroxy-2-oxopiperidine with hot aqueous barium hydroxide affords (S)-(+)-5-amino-4-hydroxypentanoic acid, a homolog of the pharmacologically interesting acid GABOB.