A Pyrone Strategy for the Synthesis of 3-Acyltetramic Acids

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Raymond C. F. Jones, Gurdip Bhalay, Jacqueline M. Patience and Pravin Patel


Abstract

The potential of pyrones as precursors to 3-acyltetramic acids is demonstrated by the conversion of 5-ethoxycarbonyl-4-methoxy-6-methyl-2-pyrone into a 3-acyltetramic acid.


References

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