Bioinspired Synthesis of (+)-Cinchonidine Using Cascade Reactions
| Autor: | Wentao Liu, Fei Xue, Wenfang Qin, Xiao-Yu Liu, Yong Qin, Xiaobei Wang |
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| Rok vydání: | 2018 |
| Předmět: |
Indole test
Indoles Free Radicals Light 010405 organic chemistry Cinchona Alkaloids Quinoline Enantioselective synthesis Total synthesis Stereoisomerism General Chemistry General Medicine 010402 general chemistry Combinatorial chemistry Chemical synthesis 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Cascade reaction Cascade Quinolines Cinchonidine Oxidation-Reduction |
| Zdroj: | Angewandte Chemie (International ed. in English). 57(38) |
| ISSN: | 1521-3773 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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