1341221-98-4Relevant articles and documents
Total synthesis of gelsemoxonine
Shimokawa, Jun,Harada, Takaaki,Yokoshima, Satoshi,Fukuyama, Tohru
supporting information; experimental part, p. 17634 - 17637 (2011/12/16)
The first total synthesis of gelsemoxonine (1) has been accomplished. Divinylcyclopropane-cycloheptadiene rearrangement of the highly functionalized substrate was successfully applied to assemble 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 the TMSCN-DBU reagent combination allowed a facile diastereoselective introduction of the latent nitrogen functionality of the unique azetidine moiety.