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Synthesis of Ring-Fused, N‑Substituted 4‑Quinolinones Using pKa‑Guided, Base-Promoted Annulations with Isatoic Anhydrides: Total Synthesis of Penicinotam
journal contribution
posted on 2019-12-13, 16:34 authored by Muhammad
M. Khalifa, Satish Chandra Philkhana, Jennifer E. GoldenAn anionic annulation strategy employing isatoic anhydrides
and
a wide assortment of enolizable partners was developed to afford over
80 novel ring-fused, N-substituted 4-quinolinones, an underrepresented
privileged template. Multiple factors governing the efficiency of
the transformation were determined, resulting in a reliable and tunable
synthetic platform applicable for a broad range of substrates with
variable deprotonation susceptibility, such as tetramic and tetronic
acids, cyclic 1,3-diketones, and cycloalkanones. Application to the
synthesis of bioactive, pyrrolizine-fused 4-quinolinone, penicinotam 3, resulted in the most brief and highest yielding total synthesis
of the alkaloid in three steps and a 36% overall yield.
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annulation strategyalkaloidtetronic acidstunableN-substituted 4- quinolinonesp Ktetramicsubstrateisatoic anhydridesapplicationpyrrolizine-fused 4- quinolinoneplatformQuinolinoneMultiple factorsdiketonetemplatetransformationRing-Fusedcycloalkanoneenolizable partnersefficiencydeprotonation susceptibilityassortmentBase-Promoted AnnulationsPenicinotamIsatoic AnhydridescyclicbioactiveGuidedTotal Synthesispenicinotam 380 novel ring-fusedsynthesis
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