Bioinspired Synthesis of Glycinoeclepin A Enables Chemical Interrogation of Its Plausible Biogenesis
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A bioinspired synthesis of glycinoeclepin A—the most potent hatching stimulus for the soybean cyst nematode—has been achieved from commercially available γ-oryzanol. The route features three key transformations: TFDO-directed sp³ C–H oxidation coupled with side-chain scission, a programmed skeletal reorganization (dyotropic rearrangement → epoxidation/Meinwald cascade), and a photo-oxidative decarbonylation. Mechanistic studies, including control experiments and comparative reactivity analysis, reveal how solvent and acid modulate competing carbocation pathways, governing the balance between methyl migration and hydride shift processes. This sequence provides a concise and scalable 17-step entry to glycinoeclepin A and advances a testable framework for understanding carbocation-driven skeletal rearrangements in the assembly of eclepin-type biogenesis.
