Total Synthesis of (±)‐Aspidophylline A |
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Authors: | Dr Weiwu Ren Dr Qian Wang Prof Dr Jieping Zhu |
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Institution: | Laboratory of Synthesis and Natural Products, Ecole Polytechnique Fédérale de Lausanne, EPFL‐SB‐ISIC‐LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch |
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Abstract: | 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‐azabicyclo3.3.1]nonane ring system. |
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Keywords: | bridged ring systems intramolecular Michael addition monoterpene indole alkaloids quaternary carbon atoms total synthesis |
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