By R.H.F Manske, H.L. Holmes
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Extra resources for Alkaloids: v. 3: Chemistry and Pharmacology
Its structure was determined by Goutarel, Janot, Prelog, and Taylor in 1950 (248). Cinchonamine gives color reactions typical of the indole alkaloids (249), and differs from all of the major cinchona bases in that it is oxidized by chromic acid to an acid, (CCVII), containing an intact quinuclidine residue, which was first obtained by the oxidation of quinamine (cf. Section V, 2). This result implies structure CCVIII for the alkaloid. ydride to diacetyl- TEE CHEYISTElY OF THE CINCHONA ALKALOIDS 51 albcinchonamine, from which by oxidation 2-@-acetoxyethyl)-indole-laldehyde (CCIX) w a ~obtained.
THE CHEMISTBY OF TEE CINCHONA ALKALOIDS 21 bases are represented by a-isoquinine (112, 117) and p-isoquinine (112, 118) while quinidine leads to apoquinidine methyl ether (112) and neoisoquinidine (112). 3 (cf. Section 111, 1). Ozonization of the Ar(lo)-bsaeeproceeds abnormally, and leads to 3-acetyl derivatives (119). In the quinidine series, a third unsaturated base, +quinidine (112), is known, which is hydrogenated to the same mixture of dihydro bsesa 88 that obtained from apoquinidine methyl ether and neoisoquinidine.
An important contribution to the synthetic problem was made in 1921 by E. Koenigs and Ottmann (204),who extended previous work by Rabe and Kindler (205),on the preparation of 8-(4-piperidyl)-propionic acid (CLXVIII), to the synthesis of dl-homocincholoipon (CLXXII). 8-Collidine (CLXIX) was condensed with chloral, and an intermediate (CLXX) was obtained which yielded @-(3-ethylpyridyl)-4-acrylicacid (CLXXI) on alkaline hydrolysis. Reduction of this product with sodium and amyl alcohol furnished a mixture from which dl-homocincholoipon (CLXXII) could be isolated.
Alkaloids: v. 3: Chemistry and Pharmacology by R.H.F Manske, H.L. Holmes