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

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• 作者：Donghui Ma ; Zhuliang Zhong ; Zaimin Liu ; Mingjie Zhang ; Shiyan Xu ; Dengyu Xu ; Dengpeng Song ; Xingang Xie ; Xuegong She
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：18
• 期：17
• 页码：4328-4331
• 全文大小：407K
• 年卷期：0
• ISSN：1523-7052

文摘

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.