Bioinspired Synthesis of (+)‐Cinchonidine Using Cascade Reactions |
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Authors: | Wentao Liu Wenfang Qin Xiaobei Wang Dr Fei Xue Prof Xiao‐Yu Liu Prof Yong Qin |
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Institution: | 1. School of Pharmaceutic Science, Chongqing University, Chongqing, P. R. China;2. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, and Sichuan Engineering Laboratory for Plant-Sourced Drug and Research Center for Drug Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, P. R. China |
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Abstract: | The development of efficient syntheses of complex natural products has long been a major challenge in synthetic chemistry. Designing cascade reactions and employing bioinspired transformations are an important and reliable means of achieving this goal. Presented here is a combination of these two strategies, which allow efficient asymmetric synthesis of the cinchona alkaloid (+)‐cinchonidine. The key steps of this synthesis are a controllable, visible‐light‐induced photoredox radical cascade reaction to efficiently access the tetracyclic monoterpenoid indole alkaloid core, as well as a practical biomimetic cascade rearrangement for the indole to quinoline transformation. The use of stereoselective chemical transformations in this work makes it an efficient synthesis of (+)‐cinchonidine. |
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Keywords: | alkaloids cascade reactions heterocycles photochemistry total synthesis |
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