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Total synthesis of the akuammiline alkaloid picrinine.

  • Author(s): Smith, Joel M
  • Moreno, Jesus
  • Boal, Ben W
  • Garg, Neil K
  • et al.

Published Web Location

https://doi.org/10.1021/ja501780w
Abstract

We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product's carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.

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