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  • Title: Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids.
    Author: Yang W, Sun X, Yu W, Rai R, Deschamps JR, Mitchell LA, Jiang C, MacKerell AD, Xue F.
    Journal: Org Lett; 2015 Jun 19; 17(12):3070-3. PubMed ID: 26043081.
    Abstract:
    A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.
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