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 (70°C) sigmatropic rearrangement of the compound shown below (R=protecting group) (J. Am. Chem. Soc. 2011, 133, 17634-17637). Me, Sio `N-OMe RO

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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 (70°C) sigmatropic rearrangement of the compound shown below (R=protecting group) (J. Am. Chem. Soc. 2011, 133, 17634–17637).

 

 

Draw the curved arrows for the mechanism of the formation of gelsemoxonine. Include lone pairs in your answer.  

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 (70°C) sigmatropic rearrangement of the compound shown below
(R=protecting group) (J. Am. Chem. Soc. 2011, 133, 17634-17637).
`N-OMe
Me, Sio
RO
Transcribed Image Text: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 (70°C) sigmatropic rearrangement of the compound shown below (R=protecting group) (J. Am. Chem. Soc. 2011, 133, 17634-17637). `N-OMe Me, Sio RO
X Incorrect. Identify the sigmatropic rearrangement.
Draw the curved arrows for the mechanism of the formation of gelsemoxonine. Include lone pairs in your answer.
CH,
H,C.
H,C
H,C
H,C
ČH,
Edit Drawing
Transcribed Image Text:X Incorrect. Identify the sigmatropic rearrangement. Draw the curved arrows for the mechanism of the formation of gelsemoxonine. Include lone pairs in your answer. CH, H,C. H,C H,C H,C ČH, Edit Drawing
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