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Total Synthesis of Aspidofractinine Alkaloid Paucidirinine

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journal contribution
posted on 18.12.2018, 00:00 by Weiwei Zhang, Shanhao Lin, Chenglong Du, Shangbiao Feng, Zaimin Liu, Jing Zhang, Xingang Xie, Xiaolei Wang, Huilin Li, Xuegong She
The first total synthesis of paucidirinine (1d), a highly congested aspidofractinine alkaloid containing a special contracted five-membered lactam ring, was achieved in 10 steps with 8% overall yield from commercially available materials. Several key maneuvers, including tandem enamination/[4 + 2] cycloaddition reaction and SmI2-promoted radical cyclization, were featured in this potentially scalable strategy.