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

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

1974-03-18

1976-12-14

Sutto, Anton H.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603409, C07D31300, C07D31724

Patent

active

039975681

ABSTRACT:
(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.

REFERENCES:
patent: 3852307 (1974-12-01), Urry

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