The strobilurins and oudemansins are natural β‐methoxyacrylates which inhibit mitochondrial respiration and, as a result, have fungicidal activity. A knowledge of the structures (configuration and conformation) and properties of these compounds has allowed the preparation of analogues in which both fungicidal activity and stability have been improved.

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Three routes to 6-(trifluoromethyl)pyrid-2-one involving de noWo synthesis of the pyridine ring have been investigated which would potentially allow rapid semi-technical scale manufacture. A route starting from ethyl 4,4,4-trifluoroacetoacetate (β-keto ester route) has been demonstrated. Development of the route was attempted; however, poor yields at a number of stages and scale-up difficulties made this route unattractive for commercial use. A four-stage route starting from trifluoroacetic anhydride and an alkyl vinyl ether (TFAA route) has been developed which gives good yields and productivity for all stages. The final stage of this route is a difficult decarboxylation of a nicotinic acid derivative, but an 80% yield of the required pyridone with a purity of >99.5% could be achieved without a separate purification stage. The route was scaled up to 2000 L, and several hundred kilograms of product was prepared.

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