Using alpha and beta Epimerizations of cis-2, 3-Bis (hydroxymethyl)-gamma- butyrolactone for the Synthesis of Both Enantiomers of Enterolactone

In the context of asymmetric synthesis, epimerization is usually problematic. Here, we describe the use of the epimerization of cis-2,3-bis(hydroxymethyl)-γ-butyrolactone for the synthesis of enterolactones with anti-carcinogenic, anti-inflammatory, anti-angiogenic, and antioxidant activity. Selective α- or β[1]epimerization of a γ-butyrolactone was used to selectively synthesize both enantiomers of enterolactone. Theoretical and kinetic studies were performed to elucidate the epimerization mechanism.

Author(s): Takeyuki Suzuki

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