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Total synthesis of (±)-aspidophylline A.

Ren, Weiwu; Wang, Qian; Zhu, Jieping.
Angew Chem Int Ed Engl; 53(7): 1818-21, 2014 Feb 10.
Artigo em Inglês | MEDLINE | ID: mdl-24452861
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.
Selo DaSilva