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Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
Rekke forfattare: 52019 (engelsk)Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 35, s. 6016-6023Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2019. nr 35, s. 6016-6023
Emneord [en]
Total synthesis, Asymmetric catalysis, Quinidine, Enantioselectivity, Cinchona alkaloids
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Identifikatorer
URN: urn:nbn:se:su:diva-172994DOI: 10.1002/ejoc.201901003ISI: 000482413000001OAI: oai:DiVA.org:su-172994DiVA, id: diva2:1355174
Tilgjengelig fra: 2019-09-27 Laget: 2019-09-27 Sist oppdatert: 2020-01-15bibliografisk kontrollert

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