Conversion of (10'S)-zearalenone to (10'R)-zearalanone

摘要

(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.