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- Title
Total synthesis of gelsemoxonine.
- Authors
Shimokawa, Jun; Harada, Takaaki; Yokoshima, Satoshi; Fukuyama, Tohru
- 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.
- Subjects
INDOLE alkaloid synthesis; VINYLCYCLOPROPANES; CYCLOHEPTADIENES; REARRANGEMENTS (Chemistry); ALKALOID synthesis; ISOMERIZATION; CHEMICAL reagents; REACTIVITY (Chemistry)
- Publication
Pure & Applied Chemistry, 2012, Vol 84, Issue 7, p1643
- ISSN
0033-4545
- Publication type
Article
- DOI
10.1351/PAC-CON-11-10-25