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The first biomimetic conversion of a germacrolide-4-epoxide into a xanthanolide
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1986
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Novel OrganocatalystsBioorganic ChemistryEngineeringBiochemistryHeterocyclicNatural SciencesBiocatalysisNatural Product BiosynthesisOrganic ChemistryCatalysisBoron TrifluorideChemistryGermacrolide-4-epoxide DihydroparthenolideNatural Product SynthesisEnantioselective SynthesisBiomolecular EngineeringFirst Biomimetic Conversion
Boron trifluoride catalysed cyclization of the germacrolide-4-epoxide dihydroparthenolide (1) provided two known guaianolides and the xanthanolide (4), the latter transformation representing the first biomimetic conversion of a germacrolide into a xanthanolide.