Efficient Total Synthesis of (S)‐14‐Azacamptothecin |
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Authors: | Guan‐Sai Liu Yuan‐Shan Yao Peng Xu Shaozhong Wang Dr Zhu‐Jun Yao Prof Dr |
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Institution: | 1. Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, 22 Hankou Road, Nanjing, Jiangsu 210093 (China);2. Joint Laboratory of Green Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China) |
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Abstract: | An efficient total synthesis of (S)‐14‐azacamptothecin has been accomplished in 10 steps and 56 % overall yield from 5H‐pyrano4,3‐d]pyrimidine 8 . A mild Hendrickson reagent‐triggered intramolecular cascade cyclization, a highly enantioselective dihydroxylation, and an efficient palladium‐catalyzed transformation of an O‐allyl into N‐allyl group are the key steps in the synthesis. This work provides a much higher overall yield than the previous achievement and shows sound flexibility for the further applications that will lead to new bioactive analogues. |
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Keywords: | 14‐azacamptothecin allyl migration asymmetric dihydroxylation cyclization total synthesis |
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