Enantioselective Biomimetic Total Syntheses of Kuwanons I and J and Brosimones A and B |
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| Authors: | Jianguang Han Xia Li Yong Guan Wenjun Zhao Prof. Dr. William D. Wulff Prof. Dr. Xiaoguang Lei |
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| Affiliation: | 1. School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072 (China);2. Department of Chemistry, Michigan State University, East Lansing, MI 48824 (USA);3. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Synthetic and Functional Biomolecules Center, and Peking‐Tsinghua Center for Life Sciences, Peking University, Beijing 100871 (China) http://www.chem.pku.edu.cn/leigroup/;4. National Institute of Biological Sciences, Beijing (NIBS), Changping District, Beijing 102206 (China) |
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| Abstract: | The first enantioselective total syntheses of prenylflavonoid Diels–Alder natural products (?)‐kuwanon I, (+)‐kuwanon J, (?)‐brosimone A, and (?)‐brosimone B have been accomplished from a common intermediate based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis‐inspired asymmetric Diels–Alder cycloaddition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration to realize a biomimetic dehydrogenation for generation of the required diene precursor. Furthermore, a remarkable tandem inter‐/intramolecular asymmetric Diels–Alder cycloaddition process was applied for the synthesis of (?)‐brosimone A. |
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| Keywords: | boron cyclization natural products synthetic methods total synthesis |
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