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Total synthesis of (±)-aspidophylline A.
Journal article

Total synthesis of (±)-aspidophylline A.

  • Ren W Laboratory of Synthesis and Natural Products, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch.
  • Wang Q
  • Zhu J
  • 2014-01-24
Published in:
  • Angewandte Chemie (International ed. in English). - 2014
bridged ring systems
intramolecular Michael addition
monoterpene indole alkaloids
quaternary carbon atoms
total synthesis
Heterocyclic Compounds, 4 or More Rings
Stereoisomerism
English 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.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/16165
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