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“…This article describes the discovery and use of the South American cinchona bark and its main therapeutic (and toxic) alkaloids, quinine and quinidine. …”
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“…The reaction is efficiently catalyzed by cinchona alkaloids, achieving high enantioselectivities and total diastereoselectivity. …”
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“…In contrast to the parent Cinchona alkaloids, azaquindoles selectively inhibit starvation‐ and rapamycin‐induced autophagy by targeting the lipid kinase VPS34.…”
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“…N-benzyl­cinchonidinium bromide, C(26)H(29)N(2)O(+)·Br(−), with the systematic name (R)-[(2S,4S,5R)-1-benzyl-5-ethenyl-1-azoniabi­cyclo­[2.2.2]octan-2-yl](quinolin-4-yl)­methanol bromide, is a quaternary ammonium salt of the cinchona alkaloid cinchonidine. This salt is widely used as a chiral phase-transfer catalyst and chiral resolution agent. …”
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“…[Image: see text] A new enantioselective peroxidation of α,β-unsaturated nitroalkenes was realized with an easily accessible acid–base bifunctional organic catalyst derived from cinchona alkaloids. This reaction provides unprecedented easy access to optically active chiral peroxides, as illustrated by the asymmetric synthesis of β-peroxy nitro compounds.…”
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“…The genus Cinchona is known for a range of alkaloids, such as quinine, quinidine, cinchonine, and cinchonidine. …”
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“…A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alkaloids allows obtaining the target products in good yields and with moderate enantioselectivities up to er = 76:24 under operationally simple conditions.…”
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“…Key to success was the use of a free OH-containing cinchona alkaloid ammonium salt catalyst and carefully optimized liquid/liquid reaction conditions. …”
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“…An unprecedented highly diastereoselective and enantioselective aldol reaction of α-alkyl azlactones and aliphatic aldehydes was achieved with cinchona alkaloid catalysts. To our knowledge, this reaction provides the first useful catalytic asymmetric access toward β-hydroxy-α-amino acids bearing alkyl substituents, which are structural motifs embedded in many natural products.…”
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“…The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented.…”
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“…The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.…”
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“…Since our ancestors began trading several millennia ago, counterfeit and substandard medicines have been a recurring problem, with history punctuated by crises in the supply of anti-microbials, such as fake cinchona bark in the 1600s and fake quinine in the 1800s. …”
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“…The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag(2)O and cinchona-derived amino phosphines applied to the synthesis of (–)- and (+)-chloramphenicol is described. …”
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“…[Image: see text] The use of Cinchona alkaloid-based chiral ammonium ylides allows for the first highly enantioselective and broadly applicable spirocyclopropanation reactions of para-quinone methides. …”
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“…In addition, the latter strategy could also be carried out with modest enantioselectivities when using simple cinchona alkaloid catalysts, albeit with relatively low yields.…”
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“…We herein report the enantioselective electrophilic α-selenation of azlactones (masked α-amino acid derivatives) and isoxazolidin-5-ones (masked β-amino acids) using Cinchona alkaloids as easily accessible organocatalysts. …”
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“…(native to tropical America), a common avenue tree of India, yields a bark drug, used as antipyretic, bitter tonic, astringent, and occasionally as a substitute for Cinchona. The district characteristics of the species are : blackish brown colour; cracks and fissures with both clean cut and thick recurved edges; irregular wrinkles; splintery and fibrous fractures; bitter taste; compound sieve plates; mostly biseriate rays; abundant rhomboidal crystals; presence of tannin, saponin, lignin and absence of alkaloids.…”
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“…The combination of cinchona-alkaloid-derived primary amine and Au(I)–phosphine catalysts allowed the selective C—H functionalization of two adjacent carbon atoms of pyrroles under mild reaction conditions. …”
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“…Inquiring into the causes of the global ‘spread’ of American remedies, it argues that medicinal plants like ipecacuanha, guaiacum, sarsaparilla, jalap root and cinchona moved with relative ease into Parisian medicine chests, Moroccan court pharmacies and Manila dispensaries alike, because of their ‘exotic’ charisma, the force of centuries-old medical habits, and the increasingly measurable effectiveness of many of these plants by the late eighteenth century. …”
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