Asymmetric Total Synthesis of Propindilactone G,Part 3: The Final Phase and Completion of the Synthesis |
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| Authors: | Xin‐Ting Liang Dr. Lin You Yuan‐He Li Hai‐Xin Yu Prof. Dr. Jia‐Hua Chen Prof. Dr. Zhen Yang |
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| Affiliation: | 1. State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, and, Department of Chemistry, Peking University, Beijing, P.?R. China;2. +86)?10‐6275‐9105;3. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen, P.?R. China;4. Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P.?R. China |
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| Abstract: | Two independent synthetic approaches were evaluated for the final phase of the asymmetric total synthesis of propindilactone G ( 1 ). The key steps that led to the completion of the asymmetric total synthesis included: 1) an intermolecular oxidative heterocoupling reaction of enolsilanes to link the core structure to the side chain; 2) an intermolecular Wittig reaction for the formation of the α,β,γ,δ‐unsaturated ester; and 3) a regio‐ and stereoselective OsO4‐catalyzed dihydroxylation of an α,β,γ,δ‐unsaturated enone, followed by an intramolecular lactonization reaction to afford the final product. These reactions enabled the synthesis of (+)‐propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)‐propindilactone G has been revised. Furthermore, the direct oxidative coupling strategy for ligation of the core of propindilactone G with its side chain may find application in the syntheses of other natural products and complex molecules. |
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| Keywords: | cross-coupling dihydroxylation enolsilanes propindilactone G total synthesis |
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