Journal article

Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations

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Publication Details

Author list: CÓRDOVA A, ZHANG K, ZHANG K, ZHANG K

Publication year: 2019

Start page: 6016

End page: 6023

Number of pages: 8

ISSN: 1434-193X

DOI: http://dx.doi.org/10.1002/ejoc.201901003

View additional information: View in Web of Science


Abstract

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.


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