O

On the next stage, the ethyl ester of N-benzoylhomomeroquinene (37.1.1.42) is condensed with the ethyl ester of 6-methoxyquinolinic acid (37.1.1.27) in the presence of sodium ethoxide to make a derivative of quinotoxin (37.1.1.43). Boiling this in hydrochloric acid results in hydrolysis of the carbethoxy and benzoyl groups, and simultaneous decarboxy-lation gives the compound (37.1.1.44). Treating this with sodium hypobromite makes an

N-bromo derivative (37.1.1.45), which is reacted with sodium ethoxide realizing the key moment of the synthesis—the transformation of the piperidine derivative to a quinuclidine derivative (37.1.1.46). Reducing the keto group in this molecule with lithium aluminum hydride gives the desired quinine (37.1.1.47) [17-22].

ch3o.

ch3o.

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