By R.H.F Manske, H.L. Holmes
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Additional resources for Alkaloids: v. 3: Chemistry and Pharmacology
C . 9 is no longer present. 4. The comparable tramformations of quinine and quinidine to quinotoxine permit a similar conclusion for this pair (77, 114). CII CIII The same conclusion ie reached through consideration of the formation of the anhydro bases; cinchonine and cinchonidine give the same cinchene (CIII), while quinene ie obtained from both quinine and quinidine (cf. Section 11, 1, b). 4, the FH Q--=-* H CIV FH 6H cv 26 XICHARD B. TURNER AND R. B. WOODWARD further conclusion may be drawn that d of.
In the preparation of these substances haloketones derived from quinoline4carboxylic acids by the diaromethane synthesis were generally used. The haloketones were then reduced to the corresponding halohydrins by the Meerwein-Pondorff procedure, and condensed with the appropriate amines (216). A very significant synthetic advance was made when Rabe and Pasternack showed in 1913 that aliphatic esters could be condensed smoothly with ethyl cinchoninate, to give 8-keto esters (CLXXXI) from R' I COCHCOOR" 45 T E E CHEMISTRY OF T E E CINCHONA ALKALOIDS (CLXXXIII).
TURNER AND R. B. WOODWARD CHO (Di)hydroxyphcnylalanime OyT 1.
Alkaloids: v. 3: Chemistry and Pharmacology by R.H.F Manske, H.L. Holmes