The total synthesis of quinine, a naturally-occurring antimalarial drug, was developed over a literary synthesis-year period.
The aromatic component of the quinine molecule is a quinoline with a methoxy substituent. 1817: First isolation of quinine from cinchona tree by Pierre Joseph Pelletier and Joseph Caventou. 1918: Paul Rabe and Karl Kindler synthesize quinine from quinotoxine, reversing the Pasteur chemistry. Woodward controversy almost a century later. 1940: Robert Burns Woodward signs on as a consultant for the Polaroid Corporation at the request of Edwin H.
Quinine is of interest to Polaroid for its literary synthesis polarizing properties. 1943: Prelog and Proštenik interconvert an allylpiperidine called homomeroquinene and quinotoxine. 1945: Woodward and Doering publish their second lengthy quinine paper. 1974: Kondo and Mori synthesize racemic vinylic gamma-lactones, a key starting material in Stork’s 2001 quinine synthesis.
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2008: Smith and Williams revisit and confirm Rabe’s d-quinotoxine to quinine route. 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. C for 10 hours in methanol with sodium methoxide liberates the piperidine group and leaving the methyl group in 5 with already all carbon and nitrogen atoms accounted for. The Total Synthesis of Quinine R. SYNTHESIS OF γ-LACTONES BY THE CONDENSATION OF 2-ALKENE-1,4-DIOLS WITH ORTHOCARBOXYLIC ESTERS Kiyosi Kondo and Fumio Mori Chemistry Letters Vol. Phrymarolin Fumito Ishibashi and Eiji Taniguchi Bulletin of the Chemical Society of Japan Vol.
Rabe-Kindler Total Synthesis of Quinine: Setting the Record Straight Jeffrey I. Doering Formal Total Synthesis of Quinine Aaron C. H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity D. This article needs additional citations for verification. However, the modern sense of «literary theory» only dates to approximately the 1950s when the structuralist linguistics of Ferdinand de Saussure began to strongly influence English language literary criticism.
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