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The First Synthesis of Coniochaetones A and (±)-B: Two Benzopyranone Derivatives
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1998
Year
First SynthesisDiversity Oriented SynthesisBenzopyranone DerivativesDerivativesBioorganic ChemistryRacemate Coniochaetone BOrganic ChemistryCascade ReactionHeterocycle ChemistryConiochaetones APharmacologyDerivative (Chemistry)Synthetic ChemistryEnantioselective SynthesisConiochaetone ANatural Product Synthesis
An efficient synthesis of coniochaetone A and of racemate coniochaetone B was achieved by a short five-step procedure from methyl-di-O-methyl-p-orsellinate. The key step is a cascade reaction of 2′-hydroxy-6′-methoxy-4′-methyl-2-(methylsulfinyl)-acetophenone with succindialdehyde in the presence of piperidine which allows the direct building of the tricyclic benzopyranone structure.