期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 44, 页码 17634-17637出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja208617c
关键词
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资金
- Ministry of Education, Culture, Sports, Science and Technology of Japan [21790009, 20002004]
- Grants-in-Aid for Scientific Research [21790009, 23590003, 20002004] Funding Source: KAKEN
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 alpha,beta-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.
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