REDUCTION AND OXIDATION REACTIONS OF CINCHONA ALKALOIDS

• Main Author: DANOVA - NIM: 20516018 , ADE
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/24957
• Institution: Institut Teknologi Bandung

<p align="justify">Cinchona alkaloids are isolated from the Cinchona trees. The basic structures of this compounds have quinoline and the bicyclic quinuclidine framework which is associated with the presence of a single bond to the carbinol group causing the structure of this compound to have many various conformations in the solution. On the other hand, Cinchona alkaloids have many functional groups and so it is needed selective of interconversion functional group reaction.The transformation of the hydroxy (OH) functional group to C9 has been widely used as an organocatalyst in asymmetric reactions for the preparation of chiral drugs. The 9-amino epi Cinchona alkaloids have been widely used in asymmetric reactions in the functionalization of compounds containing aldehyde and ketone groups. Therefore, the hydroxy group (OH) transformation of C9 via oxidation and reduction reaction was done. The synthesis of the Cinchona alkaloids 9-on had been done by using the modified oxidation method of Oppenauer to quinine yielded quinidinone in good yield and unsuccessful to dihydroquinine and also by using autooxidation through quinuclidine framing in aerobic conditions (H2O2) to quinine, dihydroquinine, cinchonidine and cinchonine yielded mixture of epimer Cinchona alkaloids 9-on. The synthesis of Hantzsch ester compounds as a source of hydrogen had been successfully performed with a low yield. Reduction reaction catalyzed by palladium (II) chloride at 2 mol%, 2.7 mol% and 2.8 mol% in pH = 4 yielded mixtures of dihydroquinine and dihydroquinidine, epi dihydroquinine and epi dihydroquinidine mixtures as well as mixtures of quinotoxine and their isomers. <p align="justify">