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| Other names | Lilly 113935; LY-113935 |
| Drug class | Nonsteroidal antiandrogen |
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| Formula | C24H26O5 |
| Molar mass | 394.467 g·mol−1 |
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Pentomone (INNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name; development codesLilly 113935 andLY-113935) is anonsteroidal antiandrogen (NSAA) described as a "prostate growth inhibitor" which was never marketed.[1] It was synthesized and assayed in 1978.[1]
Condensation of two equivalents ofo-vanillin with 4,4-dimethylcyclohexadienone (2) gives the five-ringketone derivative (3). The reaction may be visualized as initial conjugate addition ofphenoxide to the enone followed by interception of the resulting anion by the aldehyde carbonyl group.Catalytic hydrogenation then reduces botholefin pi-bonds as well as the ketone, to give (4). Re-oxidation of thealcohol thus formed withpyridinium chlorochromate affords pentomone.[2][3]