The poison gelsemoxonine can be isolated from the leaves of a plant native to
Chapter 17, Problem 17.70(choose chapter or problem)
The poison gelsemoxonine can be isolated from the leaves of a plant native to southeastern Asia (Gelsemium elegans). A key step in a synthesis of this natural product involves a thermally initiated (70C) sigmatropic rearrangement of the compound shown below (R = protecting group) (J. Am. Chem. Soc. 2011, 133, 1763417637). Predict the product of this reaction and propose a mechanism for its formation. N OMe O Me3SiO O RO
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