Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 35, Pages 6016-6023Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901003
Keywords
Total synthesis; Asymmetric catalysis; Quinidine; Enantioselectivity; Cinchona alkaloids
Categories
Funding
- European Union
- Mid Sweden University
- Swedish National Research Council
- VR
- Swedish Governmental Agency for Innovation Systems (VINNOVA)
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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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