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Bioinspired Synthesis of (+)‐Cinchonidine Using Cascade Reactions
Author(s) -
Liu Wentao,
Qin Wenfang,
Wang Xiaobei,
Xue Fei,
Liu XiaoYu,
Qin Yong
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804848
Subject(s) - cinchonidine , chemistry , enantioselective synthesis , cascade , biomimetic synthesis , quinoline , indole test , combinatorial chemistry , cascade reaction , stereoselectivity , indole alkaloid , cinchona , total synthesis , organic chemistry , catalysis , chromatography
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.