C−H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity
Abstract: 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 in vitro and in mice infected with Plasmodium berghei.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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C−H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity ; volume:57 ; number:33 ; year:2018 ; pages:10737-10741 ; extent:5
Angewandte Chemie / International edition. International edition ; 57, Heft 33 (2018), 10737-10741 (gesamt 5)
- Creator
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O' Donovan, Daniel H.
Aillard, Paul
Berger, Martin
de la Torre, Aurélien
Petkova, Desislava
Knittl‐Frank, Christian
Geerdink, Danny
Kaiser, Marcel
Maulide, Nuno
- DOI
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10.1002/anie.201804551
- URN
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urn:nbn:de:101:1-2022091207322704470096
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:24 AM CEST
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Associated
- O' Donovan, Daniel H.
- Aillard, Paul
- Berger, Martin
- de la Torre, Aurélien
- Petkova, Desislava
- Knittl‐Frank, Christian
- Geerdink, Danny
- Kaiser, Marcel
- Maulide, Nuno
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