Total Synthesis of (±)-Aspidophylline A

Ren, WeiwuWang, QianZhu, Jieping2014-02-112014-02-112014-02-11201410.1002/anie.201310929https://infoscience.epfl.ch/handle/20.500.14299/100546WOS:000330680400010A 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.bridged ring systemsintramolecular Michael additionmonoterpene indole alkaloidsquaternary carbon atomstotal synthesisTotal Synthesis of (±)-Aspidophylline Atext::journal::journal article::research article