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Protecting-Group-Free Total Synthesis of (−)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization

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journal contribution
posted on 16.08.2016, 14:38 by Donghui Ma, Zhuliang Zhong, Zaimin Liu, Mingjie Zhang, Shiyan Xu, Dengyu Xu, Dengpeng Song, Xingang Xie, Xuegong She
A protecting-group-free route for the total synthesis of (−)-lycopodine was demonstrated in only 8 steps from Wade’s fawcettimine enone (12 steps from commercial availiable (R)-(+)-pulegone). The key core of this alkaloid was constructed through a phosphoric acid promoted and highly stereocontrolled alkyne aza-Prins cyclization reaction, synchronously establishing the bridged B-ring and the C13 quaternary stereocenter. Importantly, the synthesis further features a new efficient approach for the preparation of other lycopodine-type alkaloids.