Pentomone (, ) (developmental code name Lilly 113935 or LY-113935) is a nonsteroidal antiandrogen (NSAA) described as a " prostate growth inhibitor" which was never marketed. It was synthesized and assayed in 1978.

Synthesis

Condensation of two equivalents of o-vanillin with 4,4-dimethylcyclohexadienone (2) gives the five-ring

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

derivative (3). The reaction may be visualized as initial conjugate addition of

phenoxide Phenolates (also called phenoxides) are anions, salts, and esters of phenols. They may be formed by reaction of phenols with strong base. Properties Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic s ...

to the enone followed by interception of the resulting anion by the aldehyde carbonyl group. Catalytic hydrogenation then reduces both

olefin In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

pi-bonds as well as the ketone, to give (4). Re-oxidation of the

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

thus formed with

pyridinium chlorochromate Pyridinium chlorochromate (PCC) is a yellow-orange salt (chemistry), salt with the chemical formula, formula 5H5NH rO3Cl��. It is a reagent in organic synthesis used primarily for organic redox reaction, oxidation of Alcohol (chemistry), al ...

affords pentomone.David A Hall, Richard E Heiney, & Michael E Flaugh, GB1593643 (1981 to Eli Lilly and Co).

References

Ethers Heterocyclic compounds with 5 rings Ketones Nonsteroidal antiandrogens Oxygen heterocycles Methoxy compounds {{genito-urinary-drug-stub