Abstract
Biomimetic total syntheses of potent antiviral spirooliganones A and B were achieved with 3% and 2% yield, respectively, in 12 steps from commercially available materials. The synthetic strategy was inspired primarily by the biogenetic hypothesis and was enabled by two independent cascade events: (i) an unprecedented reaction involving aromatic Claisen rearrangement/o-quinone methide formation/hetero-Diels-Alder cycloaddition to construct the tetracyclic framework and (ii) phenol oxidative dearomatization/spirocyclization to build the spiro-fused cyclohexadienone/tetrahydrofuran moiety.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology
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Biomimetics
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Chlorocebus aethiops
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Cycloaddition Reaction
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Dogs
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Indolequinones / chemistry
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Influenza A Virus, H3N2 Subtype / drug effects*
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Madin Darby Canine Kidney Cells / drug effects
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Molecular Structure
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Oxidation-Reduction
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
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Spiro Compounds / pharmacology
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Stereoisomerism
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Vero Cells / drug effects
Substances
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Antiviral Agents
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Indolequinones
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Spiro Compounds
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spirooliganone A
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quinone methide