4.7 Article

Biomimetic Domino Knoevenagel/Cycloisomerization Strategy for the Synthesis of Citridone A and Derivatives

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 12226-12236

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01542

Keywords

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Funding

  1. Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET)
  2. Agencia Nacional de Promocion Cientifica y Tecnologica (ANPCyT) [PICT-2017-2694, PICT-2018-4150]
  3. Agencia Santafesina de Ciencia, Tecnologia e Innovacion (ASACTEI) [AC - 2015-00005]
  4. Universidad Nacional de Rosario [BIO 580]
  5. Natural Sciences and Engineering Research Council of Canada (NSERC)
  6. Memorial University

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The study developed a simple method to access citridone A and related synthetic compounds, highlighting the power of domino cascades in the synthesis of natural product frameworks. This may help promote future studies on this promising new class of pyridone alkaloids.
Studies on Knoevenagel condensations between conjugated dienals and 4-hydroxy-2-pyridone/quinolone-type 1,3dicarbonyl equivalents led to the development of a simple one-pot strategy to access citridone A and related synthetic cyclopenta[b]furopyridones/quinolones. The present work highlights the power of domino cascades in the synthesis of natural product frameworks and may help promote future studies on this promising new class of pyridone alkaloids.

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