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Total synthesis of gelsemoxonine
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Abstract
The first total synthesis of gelsemoxonine has been accomplished. A divinylcyclopropane–cycloheptadiene rearrangement of the highly functionalized substrate successfully assembled the spiro-quaternary carbon center connected to the bicyclic seven-membered core structure. A one-pot isomerization reaction of the α,β-unsaturated aldehyde to the saturated ester via a trimethylsilyl cyanide–diazabicycloundecene (TMSCN–DBU) reagent combination allowed a facile and diastereoselective introduction of the latent nitrogen functionality in the unique azetidine moiety.
