4.7 Article

Total Synthesis of (-)-Canadine, (-)-Rotundine, (-)-Sinactine, and (-)-Xylopinine Using a Last-Step Enantioselective Ir-Catalyzed Hydrogenation

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JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 12, 页码 8143-8153

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00602

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  1. Fundamental Research Funds for the Central Universities [YJ201805, YJ201864]

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A concise asymmetric total synthesis of a group of tetrahydroprotoberberine alkaloids was achieved in three steps, utilizing efficient strategies for synthesis and introducing the desired stereochemistry at the C-14 position. This work significantly expedites the asymmetric synthesis of the entire tetrahydroprotoberberine alkaloid family as well as structurally related non-natural analogues.
A concise asymmetric total synthesis of a group of tetrahydroprotoberberine alkaloids, (-)-canadine, (-)-rotundine, (-)-sinactine, and (-)-xylopinine, has been accomplished in three steps from the commercially available corresponding disubstituted phenylethylamine and disubstituted benzaldehyde. Our synthesis toward these four alkaloids took advantage of the following strategy: in the first step, we achieved an efficient and sustainable synthesis of secondary amine hydrochlorides via a fully continuous flow; in the second step, we developed a Pictet-Spengler reaction/Friedel-Crafts hydroxyalkylation/dehydration cascade for the construction of the dihydroprotoberberine core structure (ABCD-ring); and in the last step, Ir-catalyzed enantioselective hydrogenation was employed for the introduction of the desired stereochemistry at the C-14 position in the tetrahydroprotoberberine alkaloids. This work significantly expedites the asymmetric synthesis of the entire tetrahydroprotoberberine alkaloid family as well as a more diverse set of structurally related non-natural analogues.

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