Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 33, Pages 10737-10741Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804551
Keywords
C-H activation; malaria; quinine; total synthesis
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Funding
- University of Vienna
- Max-Planck-Institut fur Kohlenforschung
- ERC (StG FLATOUT)
- ERC (CoG VINCAT)
- FWF (graduate program MolTag) [W1232]
- DFG [MA 4861/3-1, 4-1, 4-2]
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We report a novel approach to the classical natural product quinine that is based on two stereoselective key steps, namely a C-H activation and an aldol reaction, to unite the two heterocyclic moieties of the target molecule. This straightforward and flexible strategy enables a concise synthesis of natural (-)-quinine, the first synthesis of unnatural (+)-quinine, and also provides access to unprecedented C3-aryl analogues, which were prepared in only six steps. We additionally demonstrate that these structural analogues exhibit improved antimalarial activity compared with (-)-quinine both invitro and in mice infected with Plasmodium berghei.
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