Carbon-14 isotope is one of the most useful tool in tracking the movement of a molecule in a living system. Due to its long half-life and low energy, carbon-14 continues to be the cornerstone in the development of pharmaceutical and crop protection chemicals. The presentation will highlight the 14C-syntheses of bicyclopyrone, a HPPD class of herbicide and a metabolite of sedaxane, a SDHI fungicide. The key step in the synthesis of 14C-bicyclopyrone is the replacement of a low yielding thermolysis reaction with a phosphazene base-induced elimination of the benzenesulfonyl group to form the desired vinyl sulfone, which results in an improved and scalable synthesis. A bioinspired synthesis of a 14C-labeled sedaxane metabolite will also be discussed. The radiolabeled standards of both bicyclopyrone and the sedaxane metabolite were used in environmental fate and metabolism studies required for product registration.

Synthesis of radiolabeled standards of bicyclopyrone and sedaxane to support product development

256th National Meeting (2018)

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