Total Synthesis of the Akuammiline Alkaloid Picrinine

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• 作者：Joel M. Smith ; Jesus Moreno ; Ben W. Boal ; Neil K. Garg
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：March 26, 2014
• 年：2014
• 卷：136
• 期：12
• 页码：4504-4507
• 全文大小：310K
• 年卷期：v.136,no.12(March 26, 2014)
• ISSN：1520-5126

文摘

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鈥檚 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.