Total synthesis of the akuammiline alkaloid picrinine.
- Author(s): Smith, Joel M
- Moreno, Jesus
- Boal, Ben W
- Garg, Neil K
- et al.
Published Web Locationhttps://doi.org/10.1021/ja501780w
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.