A Concise Total Synthesis of (+)-Scholarisine A Empowered by a Unique C鈥揌 Arylation

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• 作者：Myles W. Smith ; Scott A. Snyder
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：September 4, 2013
• 年：2013
• 卷：135
• 期：35
• 页码：12964-12967
• 全文大小：300K
• 年卷期：v.135,no.35(September 4, 2013)
• ISSN：1520-5126

文摘

The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C鈥揌 arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels鈥揂lder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule鈥檚 quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone.