• Medientyp: E-Artikel
  • Titel: Pyroglutamic Acid in Drug Synthesis, Part 1 A Method for the Synthesis of Enantiomerically Pure 4‐Alkyl‐4‐arylpyroglutamic Acids
  • Beteiligte: Fleischhacker, Wilhelm; Riedl, Thomas; Völlenkle, Horst; Noe, Christian R.
  • Erschienen: Wiley, 1996
  • Erschienen in: Archiv der Pharmazie
  • Sprache: Englisch
  • DOI: 10.1002/ardp.19963290108
  • ISSN: 0365-6233; 1521-4184
  • Schlagwörter: Drug Discovery ; Pharmaceutical Science
  • Entstehung:
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>Synthesis of the title compounds is described, starting from alkylation of the pyroglutaminol‐acetal <jats:bold>4a</jats:bold><jats:sup>[1]</jats:sup> at the α‐lactam position C‐6 with methyl iodide. Subsequent addition of 2‐cyclohexen‐1‐one led to diastereoselective formation of the 1,2‐aldol addition product <jats:bold>7b/7c</jats:bold>, which after dehydratization was aromatized with DDQ to yield the 6‐methyl‐6‐phenyl derivative <jats:bold>7h.</jats:bold> Acetal cleavage and Jones oxidation yielded 4,4‐disubstituted, enantiomerically pure pyroglutamic acid <jats:bold>3b.</jats:bold> X‐ray analysis confirmed the assignment of the configuration of the newly created chiral centre.</jats:p>