A Single Enantiomer Preparation of Prozac? and a Novel Synthesis of Amides

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Several modern-day pharmaceuticals consist of molecules that are chiral. These molecules are of special importance because they are composed of enantiomers. Enantiomers are nearly identical molecules that are non-superimposable mirror images of each other. Interestingly enough, enantiomeric pairs often have different effects within the body. We are working on two ideas, the first to show that a drug such as Prozac? can be made using our process, and the second, to increase the number of functional groups on our enantiopure molecules. The anti-depressant Prozac? is a chiral drug that is composed of two enantiomers. This compound is currently prescribed as a racemate, meaning that it consists of equal amounts of the two enantiomeric forms. Although each enantiomer has anti-depressant affects within the body, it is found that the drugs (S)-enantiomer has anti-migraine properties in addition to its anti-depressant. Unfortunately, these affects are masked when the drug is taken in its racemic form. Our research proposes a method of synthesizing the pure (S)-enantiomer of Prozac? in order to unleash the molecules anti-migraine affects. In order to synthesize the molecule, a cyano group must be converted to an amide. Currently there are few ways that work to do such a conversion. We have developed mild reaction conditions to create the change and leave the stereochemistry of the molecule unchanged.


D. Deardorff




Support provided by:National Science Foundation and the Howard Hughes Medical Institute

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