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Synthesis 1986; 1986(3): 232-233
DOI: 10.1055/s-1986-31506
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Chirospecific Synthesis of (S)-(+)- and (R)-(-)-5-Amino-4-hydroxypentanoic Acid from L- and D-Glutamic Acid via (S)-(+)- and (R)-(-)-5-Hydroxy-2-oxopiperidine

C. Herdeis*
  • *Institut für Pharmazie und Lebensmittelchemie der Universität München, Sophienstraße 10, D-8000 München 2, Federal Republic of Germany
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Publication Date:
20 August 2002 (online)

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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.