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Using α- and β-Epimerizations of cis-2,3-Bis(hydroxymethyl)-γ-butyrolactone for the Synthesis of Both Enantiomers of Enterolactone
- Source :
- The Journal of Organic Chemistry; 20220101, Issue: Preprints
- Publication Year :
- 2022
-
Abstract
- 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-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.
Details
- Language :
- English
- ISSN :
- 00223263
- Issue :
- Preprints
- Database :
- Supplemental Index
- Journal :
- The Journal of Organic Chemistry
- Publication Type :
- Periodical
- Accession number :
- ejs59090848
- Full Text :
- https://doi.org/10.1021/acs.joc.1c02801