Total Synthesis of the Akuammiline Alkaloid Picrinine

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-03, Vol.136 (12), p.4504-4507
Main Authors: Smith, Joel M, Moreno, Jesus, Boal, Ben W, Garg, Neil K
Format: Article
Language:English
Subjects:
Alkaloids
Assembly
Carbon
Chemistry Techniques, Synthetic
Communication
Forges
Indole Alkaloids - chemical synthesis
Synthesis
Synthesis (chemistry)
Transformations
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja501780w