The Synthesis of trans-Flavan-3-ol Gallates by Regioselective Oxidative Etherification and Their Cytotoxicity Mediated by 67 LR

Nana Shiraishi, Motofumi Kumazoe, Shinichiro Fuse, Hirofumi Tachibana, Hiroshi Tanaka

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

We report on a chiral pool approach for the synthesis of trans-flavan-3-ol gallates from epichlorohydrin. The trans-flavan-3-ol gallates were prepared by the cycloetherification of the phenol at the C2 benzylic position of 2-acylozyl-1,3-diarylpropane during regioselective C−H oxidation. The 1,3-diarylpropanes were prepared starting from epichlorohydrin by epoxide opening with A and B ring precursors, followed by acylation of the resultant alcohol with galloyl chloride. The availability of both the enantiomers of epichlorohydrin allowed the preparation of the corresponding enantiomer using the same procedure. The cytotoxicity of the compounds against U266 cells was tested, in which 5-deoxy-7,3′-O-dimethyl gallocatechin gallate exhibited cytotoxicity that was more than ten times stronger than natural (−)-EGCG. In addition, the absolute configuration of the derivatives did not critically affect the biological activity.

Original languageEnglish
Pages (from-to)13050-13053
Number of pages4
JournalChemistry - A European Journal
Volume22
Issue number37
DOIs
Publication statusPublished - Jan 1 2016

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Epichlorohydrin
Enantiomers
Cytotoxicity
Acylation
Bioactivity
Phenols
Alcohols
Epoxy Compounds
Availability
Phenol
Derivatives
Oxidation
Chlorides
flavan-3-ol

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

The Synthesis of trans-Flavan-3-ol Gallates by Regioselective Oxidative Etherification and Their Cytotoxicity Mediated by 67 LR. / Shiraishi, Nana; Kumazoe, Motofumi; Fuse, Shinichiro; Tachibana, Hirofumi; Tanaka, Hiroshi.

In: Chemistry - A European Journal, Vol. 22, No. 37, 01.01.2016, p. 13050-13053.

Research output: Contribution to journalArticle

Shiraishi, Nana ; Kumazoe, Motofumi ; Fuse, Shinichiro ; Tachibana, Hirofumi ; Tanaka, Hiroshi. / The Synthesis of trans-Flavan-3-ol Gallates by Regioselective Oxidative Etherification and Their Cytotoxicity Mediated by 67 LR. In: Chemistry - A European Journal. 2016 ; Vol. 22, No. 37. pp. 13050-13053.
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