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By R.H.F Manske, H.L. Holmes

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The desoxy bases, of the general structure XCVIII,have usually been prepared by transformation of the cinchona alkaloids into chlorides (XCVII)by phosphorus pentachloride and removal of the halogen in the latter by metalacid combinations (64,97, 134, 135, 136). It is reported that direct removal of the hydroxyl group is brought about by electrolytic reduction (132). XCVII XCVIII 24 RICHARD B. TURNER AND R. B. WOODWARD The desoxy compounds, like other similarly constituted substances, (cf. 9 (137).

L to give quaternary salts (139). 1-oxides (140-142). It is of some interest that the vinyl group in quinine N. l-oxide can be hydrogenated without disturbance of the oxide function (140). f. Metabolic Reactions. Animal tissues appear to contain an enzyme system which catalyzes the oxidation of the cinchona alkaloids. A number of oxidation products is formed of which the 2'-hydroxy derivatives of quinine and cinchonine have been isolated and identified (143, 144). 111. Stereochemistry The first work on the stereochemistry and optical properties of the cinchona bases was undertaken by Pasteur (70, 145) in 1852.

6 CCXII 2. QUINMNEAND CONQUINAMINE The isomeric bases, quinamine and conquinamine, of the formula CIOHZ~OZNS, were isolated in 1872 and 1877 by H e w (251). 52 RICEABD B. TURNER AND R. B. WOODWABD Kirby showed that quinamine and the substances derived from it gave indole color reactions, and isolated 2,3-dimethylindolefrom zinc dust distillation of the alkaloid (252). Henry, Kirby, and Shaw oxidized quinaminewith chromic acid, and obtained the quinuclidine acid (CCVII) (253). It was thus clear that quinamine contained the vinylquinuclidine system of the major cinchona alkaloids, attached to an easily oxidizable residue, CloHloO& (cf.

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