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Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 52019 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690Article in journal (Refereed) Epub ahead of print
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.
Keywords [en]
Total synthesis, Asymmetric catalysis, Quinidine, Enantioselectivity, Cinchona alkaloids
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-172994DOI: 10.1002/ejoc.201901003ISI: 000482413000001OAI: oai:DiVA.org:su-172994DiVA, id: diva2:1355174
Available from: 2019-09-27 Created: 2019-09-27 Last updated: 2019-12-09Bibliographically approved

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