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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 23
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Original Articles

Semisynthesis of Fluoro-substituted Benzoates of Epi-gallocatechin

Xu Long Qin Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
,
Xue Min Li Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
,
Jian Yuan Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
,
Di Chen Developmental Therapeutics Program, Barbara Ann Karmanos Cancer Institute, and Department of Oncology, School of Medicine, Wayne State University, Detroit, Michigan, USA
,
Tao Jiang Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China
,
Q. Ping Dou Developmental Therapeutics Program, Barbara Ann Karmanos Cancer Institute, and Department of Oncology, School of Medicine, Wayne State University, Detroit, Michigan, USA
,
Tak Hang Chan Department of Applied Biology and Chemical Technology and the Open Laboratory for Chiral Technology, Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Polytechnic University, Hong Kong, China
&
Sheng Biao Wan Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, ChinaCorrespondence[email protected]
 show all
Pages 3524-3531 | Received 10 Jan 2011, Published online: 02 Aug 2012
 
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Abstract

In the present study, four fluoro-substituted benzoates of epi-gallocatechin (EGC) were prepared through a semisynthetic strategy, and the yield of benzylation of epi-gallocatechin gallate (−)-EGCG was improved by using freshly purified (−)-EGCG as starting material and a mild base of K2CO3. All structures of new compounds were characterized by 1H NMR, 13C NMR, high-resolution mass spectrometry, and optical rotation.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

This research is supported by Key International S&T Cooperation Projects (2009DFA32080) of the Ministry of Science and Technology of the People's Republic of China and by Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology. This project is also partly funded by the Special Fund for Marine Scientific Research in the Public Interest (201005024), and the Program for Changjiang Scholars and Innovative Research Team in University (IRT0944).

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