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The nonadrides. Part VI. Dimerisation of the C9 unit in vivo and in vitro
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1972
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Bioorganic ChemistryMolecular BiologyOrganic ChemistryChemical BiologyCellular PhysiologyRegenerative MedicineBiosynthesisPart ViBiochemistryMaleic AnhydrideGlaucanic AcidC9 UnitNatural Product SynthesisAsymmetric CatalysisCell BiologyEnantioselective SynthesisNatural SciencesMedicineSynthetic ChemistryBase-catalysed Dimerisation
But-1-enyl(methyl)maleic anhydride (4) has been synthesised and shown to act as an efficient (55% incorporation) precursor of the cyclononadienes, glauconic and glaucanic acids, in Penicillium purpurogenum. Base-catalysed dimerisation of compound (4) yields 5% of an epimer of glaucanic acid.