Total synthesis of the akuammiline alkaloid picrinine
Joel M Smith1, Jesus Moreno, Ben W Boal
1Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
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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