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Total Syntheses of Crinipellins Enabled by Cobalt‐Mediated and Palladium‐Catalyzed Intramolecular Pauson–Khand Reactions
Authors:Zhihui Huang  Dr. Jun Huang  Yongzheng Qu  Weibin Zhang  Prof. Dr. Jianxian Gong  Prof. Dr. Zhen Yang
Affiliation:1. State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen, China;2. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering, Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, China
Abstract:Efficient total syntheses of the naturally occurring, potent antibiotic compounds (?)‐crinipellin A and (?)‐crinipellin B are described. The key advanced intermediate, a fully functionalized tetraquinane core, was constructed by a novel thiourea/palladium‐catalyzed Pauson–Khand reaction. This intermediate can serve as a common intermediate for the collective total synthesis of other members of the crinipellin family.
Keywords:asymmetric synthesis  natural products  palladium  Pauson–  Khand reaction  quaternary carbon centers
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