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Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations
Stockholm University, Stockholm.
Stockholm University, Stockholm.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Stockholm University, Stockholm.
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2019 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 35, p. 6016-6023Article in journal (Refereed) Published
Abstract [en]

A catalytic asymmetric strategy for the total synthesis of quinuclidine natural products, which includes the completed enantioselective synthesis of the classical targets quinine and quinidine is disclosed. It is based on catalytic asymmetric cascade transformations, which paves the road for the synthesis of both enantiomers of the crucial C4 stereocenter with high enantioselectivity (up to 99 % ee) in one pot. Next, developing a route to all possible stereoisomers of a common early-stage intermediate sets the stage for the total synthesis of different enantiomers or epimers of quinine, quinidine and analogues with high selectivity. 

Place, publisher, year, edition, pages
2019. no 35, p. 6016-6023
Keywords [en]
Asymmetric catalysis, Cinchona alkaloids, Enantioselectivity, Quinidine, Total synthesis
National Category
Chemical Engineering
Identifiers
URN: urn:nbn:se:miun:diva-37014DOI: 10.1002/ejoc.201901003ISI: 000482413000001Scopus ID: 2-s2.0-85070879892OAI: oai:DiVA.org:miun-37014DiVA, id: diva2:1347861
Available from: 2019-09-02 Created: 2019-09-02 Last updated: 2019-10-16Bibliographically approved

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Zhang, KeihangCórdova, Armando

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