4.7 Article

Using α- and β-Epimerizations of cis-2,3-Bis(hydroxymethyl)-γ-butyrolactone for the Synthesis of Both Enantiomers of Enterolactone

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 8, 页码 5051-5056

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02801

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资金

  1. JSPS KAKENHI [26410047, 17K05784, 20K05494]
  2. Uehara Memorial Foundation
  3. Network Joint Research Center for Materials and Devices grant from the Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials program of the Japanese Ministry of Education, Culture, Sports, Science and Technology (MEXT) [20194015]
  4. Grants-in-Aid for Scientific Research [26410047, 17K05784, 20K05494] Funding Source: KAKEN

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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.
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.

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