Literature DB >> 15141082

Oligomeric catechins: an enabling synthetic strategy by orthogonal activation and C(8) protection.

Ken Ohmori1, Naoko Ushimaru, Keisuke Suzuki.   

Abstract

Controlled formation of oligomeric catechins has become possible by an orthogonal synthetic strategy. Bromo-capping of the C(8) position of the flavan skeleton enabled the equimolar coupling of electrophilic and nucleophilic catechin derivatives, enabling an efficient synthetic strategy to complex catechin oligomers.

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Year:  2004        PMID： 15141082      PMCID： PMC514424          DOI： 10.1073/pnas.0401651101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  5 in total

Review 1.  Oligomeric proanthocyanidins: naturally occurring O-heterocycles.

Authors:  D Ferreira; X C Li
Journal:  Nat Prod Rep       Date:  2000-04       Impact factor: 13.423

2.  Studies in polyphenol chemistry and bioactivity. 2. Establishment of interflavan linkage regio- and stereochemistry by oxidative degradation of an O-alkylated derivative of procyanidin B2 to (R)-(-)-2,4-diphenylbutyric acid.

Authors:  A P Kozikowski; W Tückmantel; C George
Journal:  J Org Chem       Date:  2000-08-25       Impact factor: 4.354

3.  Studies in polyphenol chemistry and bioactivity. 3.(1,2) stereocontrolled synthesis of epicatechin-4alpha,8-epicatechin, an unnatural isomer of the B-type procyanidins.

Authors:  A P Kozikowski; W Tückmantel; Y Hu
Journal:  J Org Chem       Date:  2001-02-23       Impact factor: 4.354

4.  Biological evaluation of proanthocyanidin dimers and related polyphenols.

Authors:  T De Bruyne; L Pieters; M Witvrouw; E De Clercq; D Vanden Berghe; A J Vlietinck
Journal:  J Nat Prod       Date:  1999-07       Impact factor: 4.050

5.  Studies in polyphenol chemistry and bioactivity. 4.(1) Synthesis of trimeric, tetrameric, pentameric, and higher oligomeric epicatechin-derived procyanidins having all-4beta,8-interflavan connectivity and their inhibition of cancer cell growth through cell cycle arrest.

Authors:  Alan P Kozikowski; Werner Tückmantel; Gesine Böttcher; Leo J Romanczyk
Journal:  J Org Chem       Date:  2003-03-07       Impact factor: 4.354
  5 in total
  6 in total

Review 1.  Chemical synthesis of proanthocyanidins in vitro and their reactions in aging wines.

Authors:  Fei He; Qiu-Hong Pan; Ying Shi; Chang-Qing Duan
Journal:  Molecules       Date:  2008-12-04       Impact factor: 4.411

2.  Total Synthesis of Parameritannin A2, a Branched Epicatechin Tetramer with Two Double Linkages.

Authors:  Vipul V Betkekar; Keisuke Suzuki; Ken Ohmori
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-20       Impact factor: 16.823

3.  Procyanidins Negatively Affect the Activity of the Phosphatases of Regenerating Liver.

Authors:  Sven Stadlbauer; Pablo Rios; Ken Ohmori; Keisuke Suzuki; Maja Köhn
Journal:  PLoS One       Date:  2015-07-30       Impact factor: 3.240

4.  Biocatalytically oligomerized epicatechin with potent and specific anti-proliferative activity for human breast cancer cells.

Authors:  Subhalakshmi Nagarajan; Ramaswamy Nagarajan; Susan J Braunhut; Ferdinando Bruno; Donna McIntosh; Lynne Samuelson; Jayant Kumar
Journal:  Molecules       Date:  2008-11-01       Impact factor: 4.411

5.  Regioselective Synthesis of Procyanidin B6, A 4-6-Condensed (+)-Catechin Dimer, by Intramolecular Condensation.

Authors:  Yusuke Higashino; Taisuke Okamoto; Kazuki Mori; Takashi Kawasaki; Masahiro Hamada; Noriyuki Nakajima; Akiko Saito
Journal:  Molecules       Date:  2018-01-18       Impact factor: 4.411

6.  Structure-Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities.

Authors:  Yoshitomo Hamada; Syota Takano; Yoshihiro Ayano; Masahiro Tokunaga; Takahiro Koashi; Syuhei Okamoto; Syoma Doi; Masahiko Ishida; Takashi Kawasaki; Masahiro Hamada; Noriyuki Nakajima; Akiko Saito
Journal:  Molecules       Date:  2015-10-16       Impact factor: 4.411
  6 in total

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