| Literature DB >> 21980918 |
Jun Shimokawa1, Takaaki Harada, Satoshi Yokoshima, Tohru Fukuyama.
Abstract
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.Entities:
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Year: 2011 PMID： 21980918 DOI： 10.1021/ja208617c
Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419