Total Synthesis of Aspidophylline A
| Autor: | Weiwu Ren, Jieping Zhu, Qian Wang |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
monoterpene indole alkaloids
quaternary carbon atoms Indole alkaloid Chemistry Stereochemistry 010405 organic chemistry Monoterpene Total synthesis General Chemistry General Medicine Ring (chemistry) 010402 general chemistry Desymmetrization 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound Intramolecular force Michael reaction intramolecular Michael addition Organic chemistry Nonane total synthesis bridged ring systems |
| Zdroj: | Angew. Chem. Int. Ed |
| DOI: | 10.1002/anie.201310929 |
| Popis: | A total synthesis of aspidophylline A, a pentacyclic akuammiline-type monoterpene indole alkaloid, is described. The synthesis features: 1) rapid access to a fully functionalized dihydrocarbazole through the desymmetrization of readily available 2-allyl-2-(o-nitrophenyl)cyclohexane-1,3-dione; 2) an intramolecular azidoalkoxylation of an enecarbamate to install both the furoindoline ring and the azido functionality; and 3) an intramolecular Michael addition for the construction of the 2-azabicyclo[3.3.1]nonane ring system. |
| Databáze: | OpenAIRE |
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