This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the non-aromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula ##SPC1## Wherein X is an integer having a value from 0 to 6 inclusive and Y is an integer having a value from 3 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds. The compounds 6-acetoxyhexanoic acid; 2-(5-hexenoyl)-cyclohexanone; 7-keto-11-dodecenoic acid; 2-hydroxyethyl 7-keto-11-dodecenoate ethylene ketal; N,N-dimethyl 7-keto-11-dodecenamide ethylene ketal; 7-keto-11-dodecenal ethylene ketal; 9-keto-2,13-tetradecadienic acid ethylene ketal; 2-hydroxyethyl 9-keto-2,13-tetradecadienoate ethylene ketal; the sodium salt of ethyl 6-(6-keto-10-undecenyl)-.beta.-dihydroresorcylate ethylene ketal; ethyl 3-bromo-6-(6-keto-10-undecenyl)-.beta.-dihydroresorcylate ethylene ketal; ethyl 6-(6-keto-10-undecenyl)-.beta.-resorcylate ehtylene ketal; ethyl 6-(6-keto-10-undecenyl)-.beta.-resorcylate ethylene ketal dibenzyl ether; ethyl 6-(6-keto-10-hydroxyundecyl)-.beta.-resorcylate ethylene ketal dibenzyl ether; and 6-(10-hydroxy-6-keto-undecyl)-.beta.-resorcylic acid dibenzyl ether are disclosed. Methods for preparing these compounds are also disclosed.
(10'R)-Zearalanone is prepared from (10'S)-zearalenone by opening the lactone ring of the zearalenone in an alkaline medium to provide a hydroxy acid, esterifying the hydroxy acid to provide a hydroxy ester, tosylating the hydroxy ester, reacting the tosyl ester with a tetraalkyl ammonium alkyl ester to invert the (S) structure to the (R) structure, and reforming and hydrogenating the lactone to provide (10'R)-zearalanone. (10'R)-Zearalanone, when present in admixture with (10'S)-zearalanone, enhances the uterotropic activity of the latter compound.
