The Quest for Quinine: Those Who Won the Battles and Those Who Won the War
- 25 January 2005
- journal article
- review article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 44 (6) , 854-885
- https://doi.org/10.1002/anie.200400663
Abstract
For a long time, the synthesis of quinine constituted an elusive target. In 2004, which marked the 60th anniversary of the publication of the approach used by Woodward and Doering to synthesize quinine, two new stereocontrolled total syntheses of the natural product were accomplished. Together with the well‐publicized first stereocontrolled total synthesis of quinine by Stork in 2001, these publications evidence the revival of interest of organic chemists in the synthesis of this compound, once considered a miracle drug. The recently disclosed syntheses of quinine also testify in a remarkable manner the huge progress made by organic synthesis during the last three decades since the first series of partially controlled syntheses of quinine by the group of Uskokovic. Following an account of the historical importance of quinine as an antimalarial drug and a brief description of the experiments which contributed to its isolation and structural elucidation, the first reconstructions of quinine and the total syntheses of the natural product are discussed.Keywords
This publication has 292 references indexed in Scilit:
- Neue Antimalaria‐WirkstoffeAngewandte Chemie, 2003
- Resolution of enantiomers of DL‐amino acids on silica gel plates impregnated with optically pure (—)‐quinineBiomedical Chromatography, 2001
- Kekulé reüssiert – trotz PopperAngewandte Chemie, 2000
- Kekulé Escapes, Popper NotwithstandingPublished by Wiley ,2000
- Der Stand der Totalsynthese zu Beginn des 21. JahrhundertsAngewandte Chemie, 2000
- Enantiodiscrimination by a quinine-based chiral stationary phase: A computational studyChirality, 1999
- Die Konfiguration der Ephedrin‐BasenBerichte der deutschen chemischen Gesellschaft (A and B Series), 1932
- Die Totalsynthese der China‐Alkaloide Hydro‐chinin und Hydro‐chinidin (Zur Kenntnis der China‐Alka‐loide, XXV. Mitteil.)Berichte der deutschen chemischen Gesellschaft (A and B Series), 1931
- Ueber künstliche Bildung des HarnstoffsAnnalen der Physik, 1828
- Noch ein Zusatz zu Aufsatz I. und II. in diesem StückeAnnalen der Physik, 1817