Lomevactone

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Lomevactone
Clinical data
ATC code
  • None
Identifiers
  • 4-(4-Chlorophenyl)-6-methyl-3-phenyltetrahydro-2H-pyran-2-one
JSmol)
  • Clc1ccc(cc1)C2C(C(=O)OC(C)C2)c3ccccc3

Lomevactone (

psychostimulant and antidepressant which was synthesized and assayed in the 1980s, but was never marketed.[1][2]

Stereoisomers

There are eight possible

stereoisomers of lomevactone. It is the (3R,4R,6R)-form that has the psychotherapeutic properties.[3][4]

(3R,4R,6R)-Lomevactone

Synthesis

The conjugate 1,4-alkylation reaction between 4-chlorobenzylideneacetone (1) and

phenylacetonitrile (2) gives 3-(4-chlorophenyl)-5-oxo-2-phenylhexanenitrile (3). The selective reduction of the keto group to the alcohol with sodium borohydride
gives 3-(4-chlorophenyl)-5-hydroxy-2-phenylhexanenitrile (4). Hydrolysis of the nitrile to an acid gives 3-(4-chlorophenyl)-5-hydroxy-2-phenylhexanoic acid. This is followed by lactone formation completing the synthesis of lomevactone (5).

Synthesis:[5] Patents:[6][7]

References

  1. ISBN 0-412-46630-9
    .
  2. S2CID 2372145
    .
  3. ^ Axiotis, S.; Druex, J.; Perrin, M.; Royer, J. (1982). "Conformations in the tetrahydropyran-2-one ring". Tetrahedron. 38 (4): 499–504. doi:10.1016/0040-4020(82)80093-8.
  4. doi:10.1016/0223-5234(87)90266-2
    .
  5. ^ Axiotis, S. et al, Eur. J. Med. Chem.-Chim. Ther., 1981, 16, 431, 439.
  6. ^ Pierre Simon & Jacques Dreux, U.S. patent 4,287,206 (1981 to Sanofi Aventis France).
  7. ^ 시몽 삐에르 & 드로 짝끄, KR830002288 (1983).
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