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Synthesis 1991; 1991(9): 743-744
DOI: 10.1055/s-1991-26563
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A Novel Dieckmann-Type Cyclization, the Final Step of the Synthesis of a Carbacephem Derivative

Gebhard Neyer* , Ivar Ugi
  • *Institut für Organische Chemie der Technischen Universität München, D-8046 Garching, Germany
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Publication Date:
29 April 2002 (online)

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The treatment of the triacylamine, methyl 4-(dibenzoylaminocarbonylethyl)-2-oxoazetidine-1-acetate (2), with sodium bis(trimethylsilyl)amide leads to an unprecedented Dieckmann-type ring closure to form the anion of the carbacephem derivative, methyl 3-hydroxy-1-carbacephem-4-carboxylate, (3).