Literature DB >> 17107042

Total synthesis of (S)-equol.

Jennifer M Heemstra1, Sean A Kerrigan, Daniel R Doerge, William G Helferich, William A Boulanger.   

Abstract

The first enantioselective total synthesis of (S)-equol is reported. The described route relies on an Evans alkylation to form the stereocenter and an intramolecular Buchwald etherification to generate the chroman ring. Key features of this method include its brevity, its scalability, and the low cost of starting materials. [reaction: see text].

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Year:  2006        PMID： 17107042     DOI： 10.1021/ol0620444

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

Review 1.  Equol: history, chemistry, and formation.

Authors:  Kenneth D R Setchell; Carlo Clerici
Journal:  J Nutr       Date:  2010-06-02       Impact factor: 4.798

2.  The chemopreventive action of equol enantiomers in a chemically induced animal model of breast cancer.

Authors:  Nadine M Brown; Carrie A Belles; Stephanie L Lindley; Linda D Zimmer-Nechemias; Xueheng Zhao; David P Witte; Mi-Ok Kim; Kenneth D R Setchell
Journal:  Carcinogenesis       Date:  2010-01-28       Impact factor: 4.944

3.  Mechanisms enforcing the estrogen receptor β selectivity of botanical estrogens.

Authors:  Yan Jiang; Ping Gong; Zeynep Madak-Erdogan; Teresa Martin; Muthu Jeyakumar; Kathryn Carlson; Ikhlas Khan; Troy J Smillie; Amar G Chittiboyina; Sateesh C K Rotte; William G Helferich; John A Katzenellenbogen; Benita S Katzenellenbogen
Journal:  FASEB J       Date:  2013-07-23       Impact factor: 5.191

4.  Diarylpropionitrile (DPN) enantiomers: synthesis and evaluation of estrogen receptor β-selective ligands.

Authors:  Vincent M Carroll; M Jeyakumar; Kathryn E Carlson; John A Katzenellenbogen
Journal:  J Med Chem       Date:  2011-12-14       Impact factor: 7.446

5.  Supplemental dietary racemic equol has modest benefits to bone but has mild uterotropic activity in ovariectomized rats.

Authors:  Leecole L Legette; Berdine R Martin; Mohammad Shahnazari; Wang-Hee Lee; William G Helferich; Junqi Qian; David J Waters; Alireza Arabshahi; Stephen Barnes; Jo Welch; David G Bostwick; Connie M Weaver
Journal:  J Nutr       Date:  2009-08-26       Impact factor: 4.798

6.  (±)-Equol does not interact with genistein on estrogen-dependent breast tumor growth.

Authors:  Huaxin Song; Jennifer R Hughes; Russell T Turner; Urszula T Iwaniec; Daniel R Doerge; William G Helferich
Journal:  Food Chem Toxicol       Date:  2019-11-28       Impact factor: 6.023

7.  Comparative effects of R- and S-equol and implication of transactivation functions (AF-1 and AF-2) in estrogen receptor-induced transcriptional activity.

Authors:  Svitlana Shinkaruk; Charlotte Carreau; Gilles Flouriot; Catherine Bennetau-Pelissero; Mylène Potier
Journal:  Nutrients       Date:  2010-03-15       Impact factor: 5.717

8.  Transcriptomic analysis identifies gene networks regulated by estrogen receptor α (ERα) and ERβ that control distinct effects of different botanical estrogens.

Authors:  Ping Gong; Zeynep Madak-Erdogan; Jilong Li; Jianlin Cheng; C Michael Greenlief; William Helferich; John A Katzenellenbogen; Benita S Katzenellenbogen
Journal:  Nucl Recept Signal       Date:  2014-09-12

9.  To Construct an Engineered (S)-Equol Resistant E. coli for in Vitro (S)-Equol Production.

Authors:  Hailiang Li; Shaoming Mao; Huahai Chen; Liying Zhu; Wei Liu; Xin Wang; Yeshi Yin
Journal:  Front Microbiol       Date:  2018-06-04       Impact factor: 5.640
  9 in total

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