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Synthesis of isoflavones. Part V. Irigenin and tectorigenin
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1970
Year
Certain Ethoxalylation ReactionsBiosynthesisBioorganic ChemistryDerivativesBiochemistryEngineeringNatural SciencesNatural Product BiosynthesisOrganic ChemistryGeneral Ethoxalylation ProcedurePart V. IrigeninProduct RatioNatural Product SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
The general ethoxalylation procedure for the synthesis of isoflavones has been applied to the synthesis of irigenin (VII) and tectorigenin (XVI). This synthetic route also yields the isomers, ψ-irigenin (XI) and ψ-tectorigenin (XX). Information concerning the product ratio in certain ethoxalylation reactions and the relative thermodynamic stabilities of 5,6,7- and 5,7,8-trisubstituted isoflavones is discussed.