78473-71-9Relevant articles and documents
Using α- and β-Epimerizations of cis-2,3-Bis(hydroxymethyl)-γ-butyrolactone for the Synthesis of Both Enantiomers of Enterolactone
Jiang, Rui,Ismiyarto,Abe, Tsukasa,Zhou, Da-Yang,Asano, Kaori,Suzuki, Takayoshi,Sasai, Hiroaki,Suzuki, Takeyuki
, p. 5051 - 5056 (2022/03/16)
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.
Isolation and characterization of a human intestinal bacterium Eggerthella sp. CAT-1 capable of cleaving the C-Ring of (+)-catechin and (-)-Epicatechin, followed by p-dehydroxylation of the B-ring
Jin, Jong-Sik,Hattori, Masao
, p. 2252 - 2256 (2013/02/23)
We isolated a human intestinal bacterium, capable of cleaving the C-ring and dehydroxylating the Bring of both (+)-catechin (2 R ,3S ) and (-)-epicatechin (2 R ,3R). Although the strain was classified as Eggerthella (Eg.) lenta [named Eg. sp. CAT-1 (JF798636)] by 16S ribosomal RNA (rRNA) gene similarity, it was quite different in substrate specificity from a previously isolated strain, Eg. sp. SDG-2, which takes part in cleavage of the C-ring and dehydroxylation of the 3,4-dihydroxyphenyl moiety (B-ring) of (3R)-flavan-3-ol derivatives. On the other hand, both Eg. sp. CAT-1 and Eg. sp. SDG-2 showed the same substrate specificity against dehydroxylation of enantiomeric lignans, (+)- and (-)-dihydroxyenterodiol, and (+)- and (-)-dihydroxyenterolactone.
Asymmetric syntheses of (-)-enterolactone and 7′R)-7′- hydroxyenterolactone via organocatalyzed aldol reaction
Hajra, Saumen,Giri, Aswini Kumar,Hazra, Sunit
supporting information; experimental part, p. 7978 - 7981 (2010/02/28)
(Chemical Equation Presented) Short syntheses of (-)-enterolactone (1a) and (7′R)-7′-hydroxyenterolactone (1b) have been achieved utilizing organocatalyzed asymmetric cross-aldol reaction of aldehydes 2 and 3 and base-mediated alkylation of lactones 5 and 4.
