Using α- and β-Epimerizations of cis-2,3-Bis(hydroxymethyl)-γ-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 theepimerization ofcis-2,3-bis(hydroxymethyl)-gamma-butyrolactone for thesynthesis of enterolactones with anti-carcinogenic, anti-inflamma-tory, anti-angiogenic, and antioxidant activity. Selective alpha-or beta-epimerization of a gamma-butyrolactone was used to selectivelysynthesize both enantiomers of enterolactone. Theoretical and kinetic studies were performed to elucidate the epimerization mechanism.

Automated summary

In the context of asymmetric synthesis, epimerization has been a challenge. In this study, the epimerization of gamma-butyrolactone was used to synthesize enterolactones with various biological activities. The selective alpha or beta-epimerization allowed the synthesis of both enantiomers of enterolactone. The mechanism of the epimerization was elucidated through theoretical and kinetic studies.