Total Synthesis of the Antibiotic Kendomycin: A Macrocyclization Using the Tsuji–Trost Etherification |
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| Authors: | Dr. Tetsuya Sengoku Dr. Shu Xu Kenji Ogura Yoshinori Emori Kenji Kitada Prof. Dr. Daisuke Uemura Prof. Dr. Hirokazu Arimoto |
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| Affiliation: | 1. Graduate School of Life Sciences, Tohoku University, 2‐1‐1 Katahira, Sendai 980‐8577 (Japan) http://www.agri.tohoku.ac.jp/bunseki/index‐j.html;2. Current address: Department of Materials Science, Faculty of Engineering, Shizuoka University, Shizuoka 432‐8561 (Japan);3. Department of Chemistry, Faculty of Science, Kanagawa University, Hiratsuka 259‐1293 (Japan) |
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| Abstract: | A highly stereocontrolled, convergent total synthesis of kendomycin [(?)‐TAN2162], an ansa‐macrocyclic antibiotic, is reported. The key of the strategy is an unprecedented Tsuji–Trost macrocyclic etherification, followed by a transannular Claisen rearrangement to construct the 18‐membered carbocyclic framework. The oxa‐six‐ and five‐membered rings were also stereoselectively constructed respectively by a cascade oxidative cyclization at an unfunctionalized benzylic position and using a one‐pot epoxidation/5‐exo‐tet epoxide opening. |
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| Keywords: | antibiotics macrocycles natural products palladium total synthesis |
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