History and Epistemology of Science in the Classroom: The Synthesis of Quinine as a Proposal

Souza, Karina Ap. F. D.; Porto, Paulo Alves

doi:10.1021/ed1003542

Cited by 10 publications

(15 citation statements)

References 26 publications

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“…[73] Others have made similar arguments against 'quinotoxine'. [74] Nevertheless, 'quinotoxin(e)' has continued to be widely used, [14,28,[75][76][77][78][79] although some authors have 'remained faithful' to 'quinicine'. [62,65,74,80] The next episode in the nomenclature story is connected to the above-mentioned introduction of quinicine as a cerebral-vasodilating agent.…”

Section: Quinicine and Cinchonicine: Additional Workmentioning

confidence: 99%

Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids

Gál

2019

Helvetica Chimica Acta

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Pasteur carried out pioneering work on cinchona alkaloids and their derivatives and his studies led to important discoveries. He examined crystals of cinchona alkaloids for his correlation of crystal hemihedrism with molecular chirality, studies that led Pasteur to the discovery of physicochemical differences between diastereoisomeric salts of tartaric acids with optically active cinchona bases, an important insight into fundamentals of molecular chirality. These physicochemical differences also led to Pasteur’s invention of the vital method of racemate resolution through diastereoisomeric derivatives. Pasteur clarified the confusion around the cinchona alkaloids by elucidating their identities and relations. He discovered the conversion of the major cinchona alkaloids to quinicine and cinchonicine, a finding subsequently of considerable importance in studies of the structure and synthesis of the major cinchona alkaloids. The reaction producing quinicine and cinchonicine led Pasteur to the discovery of the racemization of tartaric acid and the finding of meso‐tartaric acid, fundamental breakthroughs in the development of stereochemistry.

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Section: Quinicine and Cinchonicine: Additional Workmentioning

confidence: 99%

Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids

Gál

2019

Helvetica Chimica Acta

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“…To date, more than 3000 MIAs have been identified with diverse structures and bioactivities, which are exemplified by three of the most well-known members: quinine ( 1 ), strychnine ( 2 ), and vinblastine ( 3 ) (Figure ). − Quinine ( 1 ) belongs to the family of Cinchona alkaloids and is an antimalarial drug; − strychnine ( 2 ), one of the most complex Strychnos alkaloids, is a potent toxin; − and vinblastine ( 3 ), a Vinca alkaloid, is a frontline anticancer therapeutic and one of the most expensive small-molecule, off-patent drugs on the pharmaceutical market. − …”

Section: Introductionmentioning

confidence: 99%

“…Elaboration to (−)-Secologanin and (−)-Strictosidine. As shown in Scheme 4, Diels−Alder adduct 7a was elaborated to (−)-secologanin (6). Deprotection of 7a afforded the corresponding free alcohol, which underwent elimination under standard Grieco-olefination conditions.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Lastly, global acetyl removal gave (−)-secologanin (6) in 65% yield over 2 steps. 40 Overall, (−)-secologanin (6) was accessed in nine steps from known materials.…”

Section: ■ Introductionmentioning

confidence: 99%

“…To access (−)-strictosidine (4), we turned to the late-stage enzymatic Pictet−Spengler reaction between (−)-secologanin (6) and tryptamine (5) (Scheme 5). The natural biocatalyst for this transformation, strictosidine synthase, has previously been used successfully in the laboratory setting to prepare 4.…”

Section: ■ Introductionmentioning

confidence: 99%

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Total Synthesis of (−)-Strictosidine and Interception of Aryne Natural Product Derivatives “Strictosidyne” and “Strictosamidyne”

et al. 2021

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Monoterpene indole alkaloids are a large class of natural products derived from a single biosynthetic precursor, strictosidine. We describe a synthetic approach to strictosidine that relies on a key facially selective Diels–Alder reaction between a glucosyl-modified alkene and an enal to set the C15–C20–C21 stereotriad. DFT calculations were used to examine the origin of stereoselectivity in this key step, wherein two of 16 possible isomers are predominantly formed. These calculations suggest the presence of a glucosyl unit, also inherent in the strictosidine structure, guides diastereoselectivity, with the reactive conformation of the vinyl glycoside dienophile being controlled by an exo-anomeric effect. (−)-Strictosidine was subsequently accessed using late-stage synthetic manipulations and an enzymatic Pictet–Spengler reaction. Several new natural product analogs were also accessed, including precursors to two unusual aryne natural product derivatives termed “strictosidyne” and “strictosamidyne”. These studies provide a strategy for accessing glycosylic natural products and a new platform to access monoterpene indole alkaloids and their derivatives.

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The Quinine Odyssey: A Barometer of the State of Organic Synthesis Over Centuries

Bissember

2024

Chemistry A European J

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The year 2024 marks the 80th anniversary of the landmark formal synthesis of (±)‐quinine completed by Woodward and Doering. This article examines the evolution of approaches to access this storied Cinchona alkaloid natural product which represent a microcosm the progress that has been made in organic synthesis over the past ~170 years. Seminal contributions led by Pasteur, Rabe, Woodward, Uskoković, Stork, Jacobsen, Hayashi, Maulide and others are discussed.

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History and Epistemology of Science in the Classroom: The Synthesis of Quinine as a Proposal

Cited by 10 publications

References 26 publications

Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids

Louis Pasteur, Chemist: An Account of His Studies of Cinchona Alkaloids

Total Synthesis of (−)-Strictosidine and Interception of Aryne Natural Product Derivatives “Strictosidyne” and “Strictosamidyne”

The Quinine Odyssey: A Barometer of the State of Organic Synthesis Over Centuries

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