Three novel approaches towards the synthesis of analogs of fluoxetine (prozac) were proposed and investigated as part of the research inspired organic laboratory experience. The first approach starts with the aldol reaction between acetic acid and benzaldehyde, followed by reduction of the acid, protection of the primary alcohol, mitsunobu reaction with 4-trifluoromethylphenol, and amination; the second approach used reductive amination of cinnamaldehyde followed by markovnov addition of the phenol to the enamine; and the third approach investigated allylation of benzaldehyde followed by nucleophilic aromatic substition, ozonolysis and reductive amination. All three methods achieved moderate success.

Alternative synthetic approaches to the syntheses of fluoxetin

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