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Total Synthesis of (−)-Principinol C
- Tianhao MaTianhao MaState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, 38 Xueyuan Road, Beijing 100191, ChinaMore by Tianhao Ma
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- Hao ChengHao ChengState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, 38 Xueyuan Road, Beijing 100191, ChinaMore by Hao Cheng
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- Mallesham PitchakuntlaMallesham PitchakuntlaState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, 38 Xueyuan Road, Beijing 100191, ChinaMore by Mallesham Pitchakuntla
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- Weihao MaWeihao MaState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, 38 Xueyuan Road, Beijing 100191, ChinaMore by Weihao Ma
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- Yanxing Jia*Yanxing Jia*[email protected]State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, 38 Xueyuan Road, Beijing 100191, ChinaMore by Yanxing Jia
Abstract
We have achieved the first total synthesis of (−)-principinol C, which possesses an intriguing and complex 5/7/6/5 tetracyclic skeleton with eight contiguous stereocenters. The 5/7/6/5 tetracyclic skeleton of principinol C was assembled using an intramolecular Pauson–Khand reaction as the key step. This synthetic route represents the first application of the intramolecular Pauson–Khand reaction of enyne to construct the 7,5-bicyclic ring system in natural product synthesis.
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