C−H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity

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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.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
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)

Urheber
O' Donovan, Daniel H.
Aillard, Paul
Berger, Martin
de la Torre, Aurélien
Petkova, Desislava
Knittl‐Frank, Christian
Geerdink, Danny
Kaiser, Marcel
Maulide, Nuno

DOI
10.1002/anie.201804551
URN
urn:nbn:de:101:1-2022091207322704470096
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
15.08.2025, 07:24 MESZ

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Beteiligte

  • 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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