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Quinine total synthesis timeline
- 1907: the correct atom connectivity established by Paul Rabe. [4]
- 1918: Paul Rabe and Karl Kindler synthesize quinine from quinotoxine, [5] reversing the Pasteur chemistry. The lack of experimental details in this publication would become a major issue in the Stork–Woodward controversy almost a century later.
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See all on WikipediaQuinine total synthesis - Wikipedia
The total synthesis of quinine, a naturally-occurring antimalarial drug, was developed over a 150-year period. The development of synthetic quinine is considered a milestone in organic chemistry although it has never been produced industrially as a substitute for natural occurring quinine. The … See more
The aromatic component of the quinine molecule is a quinoline with a methoxy substituent. The amine component has a quinuclidine skeleton … See more
The Stork quinine synthesis starts from chiral (S)-4-vinylbutyrolactone 1. The compound is obtained by chiral resolution and in fact, in the subsequent steps all stereogenic centers are put in place by chiral induction: the sequence does not contain See more
• Quinine Total Syntheses @ SynArchive.com
• Quinine story at Harvard.edu Link See more• 1817: First isolation of quinine from cinchona tree by Pierre Joseph Pelletier and Joseph Caventou.
• 1853: Louis Pasteur obtains quinotoxine (or quinicine in older literature) by acid-catalysed isomerization of quinine. See moreThe 1944 Woodward–Doering synthesis starts from 7-hydroxyisoquinoline 3 for the quinuclidine skeleton which is somewhat counter intuitive because one goes from a stable heterocyclic aromatic system to a completely saturated bicyclic ring. This compound (already … See more
Wikipedia text under CC-BY-SA license The Total Synthesis of Quinine | Journal of the …
WEBConcise Stereocontrolled Formal Synthesis of (±)-Quinine and Total Synthesis of (±)-7- Hydroxyquinine via Merged …
- Author: R. B. Woodward, W. E. Doering
- Publish Year: 1945
The First Stereoselective Total Synthesis of Quinine
WEBMar 17, 2001 · C−H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity. Angewandte Chemie International …
- Author: Gilbert Stork, Deqiang Niu, A. Fujimoto, Emil R. Koft, James M. Balkovec, James R. Tata, Gregory R. ...
- Publish Year: 2001
The Woodward–Doering/Rabe–Kindler Total …
WEB“The Total Synthesis of Quinine” was of far greater importance to Woodward than to Doering. Doering was the student; hence, this work was critical for him to obtain his first independent academic position. His …
Total Synthesis of Quinine by Woodward, Williams
WEBThe whole affair revolves around Woodward’s formal total synthesis of quinine, first published in 1944. His work with Doering led to an advanced intermediate, d-quinotoxine, which had been featured in a total …
Quinine steps back in time - Nature
WEBFeb 27, 2008 · The report by Robert Woodward and William Doering of the total synthesis of quinine in 1944 caused a sensation: it was hoped that the process could be scaled up as …
The Quest for Quinine: Those Who Won the Battles …
WEBJan 25, 2005 · 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 …
Rabe Rest in Peace: Confirmation of the Rabe-Kindler …
WEBThe three-step conversion of d -quinotoxine into quinine, as originally reported by Rabe and Kindler in 1918, has been experimentally verified. This conversion serves to re-affirm …
WEB1918, Paul Rabe and Karl Kindler reported the three-step conversion of d-quinotoxine into quinine. In 1944 Robert B. Woodward and William von Eggers Doering reported the total …
Gilbert Stork (1921–2017) - Nature
WEBNov 27, 2017 · Some 60 years after setting his sights on the compound, in 2001 he and his co-workers published the first stereoselective total synthesis of quinine (G. Stork et al. J. Am. Chem. Soc. 123,...
WEBFeb 7, 2012 · a stereoselective total synthesis of quinine was achieved by Uskokovic´, Gutzwiller, and their collaborators at Hoffmann-La Roche.8 That impressive …
WEBProblem #1. Provide a mechanism for the following transformation, including a 3-D structure that accounts for the selectivity of the chlorination. CO2Me. Fragment Coupling and …
WEBFeb 14, 2012 · 1907: The correct connectivity is “unraveled” by Rabe. 1918: Rabe and Kindler synthesize quinine from quinotoxine. 1944: Woodward and Doering synthesize …
C−H Activation Enables a Concise Total Synthesis of Quinine and ...
WEBThis straightforward and flexible strategy enables a concise synthesis of natural (−)-quinine, the first synthesis of unnatural (+)-quinine, and also provides access to …
Organocatalyst-mediated five-pot synthesis of (–)-quinine
WEBDec 7, 2022 · In this work, the enantioselective total synthesis of (–)-quinine has been accomplished in a pot-economical manner using five reaction vessels.
The Woodward-Doering/Rabe-Kindler total synthesis of quinine: …
WEBIn 1918, Paul Rabe and Karl Kindler reported the three-step conversion of d-quinotoxine into quinine. In 1944 Robert B. Woodward and William von Eggers Doering reported the total …
Total synthesis of quinine and quinidine. II | Journal of the …
WEBMay 1, 2002 · Scope of Stereoselective Mn-Mediated Radical Addition to Chiral Hydrazones and Application in a Formal Synthesis of Quinine. The Journal of Organic Chemistry …
Rabe Rest in Peace: Confirmation of the Rabe–Kindler …
WEBFeb 11, 2008 · Put to rest: The three-step conversion of d -quinotoxine into quinine, as originally reported by Rabe and Kindler in 1918, has been experimentally verified. This …
Early and Late Steps of Quinine Biosynthesis | Organic Letters
WEBFeb 24, 2021 · Although the total synthesis of quinine has been achieved, the enzymes of this biosynthetic pathway remain undiscovered. In the present work, we combined …
6.5: Quinine - Chemistry LibreTexts
WEBMar 23, 2021 · Total syntheses of the subtarget ethyl quininate (359) were also known when the total synthesis of 337 was undertaken. A particularly effective route introduces the …
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