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 language | English |
|---|---|
| Pages (from-to) | 13050-13053 |
| Number of pages | 4 |
| Journal | Chemistry - A European Journal |
| Volume | 22 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - Jan 1 2016 |
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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 journal › Article
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TY - JOUR
T1 - The Synthesis of trans-Flavan-3-ol Gallates by Regioselective Oxidative Etherification and Their Cytotoxicity Mediated by 67 LR
AU - Shiraishi, Nana
AU - Kumazoe, Motofumi
AU - Fuse, Shinichiro
AU - Tachibana, Hirofumi
AU - Tanaka, Hiroshi
PY - 2016/1/1
Y1 - 2016/1/1
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=84984992173&partnerID=8YFLogxK
U2 - 10.1002/chem.201602817
DO - 10.1002/chem.201602817
M3 - Article
C2 - 27410248
AN - SCOPUS:84984992173
VL - 22
SP - 13050
EP - 13053
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 37
ER -