325ChemInform Abstract Treatment of quinidine (I) with anhydrous AcOH (a mixture of glacial AcOH and Ac2O) gives rise to N-acetyl quinotoxine enol acetates (IIa)/(IIb) whereas the treatment with aqueous AcOH under anaerobic conditions effects an epimerization at C-9 yielding the desired epi-quinidine (III); quinotoxine (IV) is additionally formed. However, the same reaction with catalytic amounts of H2O2 (aerobic conditions) yields only the oxidation products (V). Glacial acetic acid (without addition of Ac2O) catalyzes a slow conversion of (I) to the epi-compound (III) as major product. Similar results are obtained using other cinchona alkaloids such as (VI) (quinine), (VII) (hydroquinidine), and (VIII). -The mechanisms involved in the reactions are discussed in detail (in part no yields given).
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