Lomevactone

Lomevactone is a drug described as a psychostimulant and antidepressant which was synthesized and assayed in the 1980s, but was never marketed.

Stereoisomers

There are eight possible stereoisomers of lomevactone. It is the -form that has the psychotherapeutic properties.

Synthesis

The conjugate 1,4-alkylation reaction between 4-chlorobenzylideneacetone and phenylacetonitrile gives 3--5-oxo-2-phenylhexanenitrile. The selective reduction of the keto group to the alcohol with sodium borohydride gives 3--5-hydroxy-2-phenylhexanenitrile. Hydrolysis of the nitrile to an acid gives 3--5-hydroxy-2-phenylhexanoic acid. This is followed by lactone formation completing the synthesis of lomevactone.