Alkaloids: v. 3: Chemistry and Pharmacology by R.H.F Manske, H.L. Holmes

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

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TURNER AND R. B. WOODWARD CHO (Di)hydroxyphcnylalanime OyT 1.

Except in the cases of cinchonamine, quinamine, and conquinamine little is known of most of these alkaloids beyond their empirical formulae, and the status of some of them as chemical individuals may be open to question. 1. CINCHONAMINE b a u d first isolated cinchonamine, in 1881, and showed that it possessea the formula CIBHIION,(244-247). 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.

B. WOODWARD Catalytic hydrogenation of the carbonyl group in the presence of palladium gave dihydroquinine, identical in all respects with the naturally occurring alkaloid. In addition, dihydroquinidine and a stereoisomer, subsequently identified as epidihydroquinidine (154, 155), were also isolated. Further examination of the reduction mixture revealed the presence of epidihydroquinine, and it was shown that the four isomers are likewise formed in the reduction of dihydroquinidinone with a mixture of aluminum, sodium ethoxide and alcohol.

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