Enantioselective Total Syntheses of (+)‐Gallocatechin, (−)‐Epigallocatechin, and 8‐C‐Ascorbyl‐(−)‐epigallocatechin

Chemistry – An Asian JournalVolume 8, Issue 4 p. 700-704 Communication Enantioselective Total Syntheses of (+)-Gallocatechin, (−)-Epigallocatechin, and 8-C-Ascorbyl-(−)-epigallocatechin Dr. Guang Lin, Dr. Guang Lin Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this authorDr. Le Chang, Dr. Le Chang Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055 (China), Fax: (+86) 755-2603-3174Search for more papers by this authorDr. Yongxiang Liu, Dr. Yongxiang Liu Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this authorDr. Zheng Xiang, Dr. Zheng Xiang Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this authorProf. Dr. Jiahua Chen, Corresponding Author Prof. Dr. Jiahua Chen zyang@pku.edu.cn Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this authorProf. Dr. Zhen Yang, Corresponding Author Prof. Dr. Zhen Yang zyang@pku.edu.cn Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105 Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055 (China), Fax: (+86) 755-2603-3174Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this author Dr. Guang Lin, Dr. Guang Lin Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this authorDr. Le Chang, Dr. Le Chang Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055 (China), Fax: (+86) 755-2603-3174Search for more papers by this authorDr. Yongxiang Liu, Dr. Yongxiang Liu Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this authorDr. Zheng Xiang, Dr. Zheng Xiang Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this authorProf. Dr. Jiahua Chen, Corresponding Author Prof. Dr. Jiahua Chen zyang@pku.edu.cn Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this authorProf. Dr. Zhen Yang, Corresponding Author Prof. Dr. Zhen Yang zyang@pku.edu.cn Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105 Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055 (China), Fax: (+86) 755-2603-3174Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Department of Chemistry, Peking University, 202 Chengfu Road, Beijing 100871 (China), Fax: (+86) 10-6275-9105Search for more papers by this author First published: 29 January 2013 https://doi.org/10.1002/asia.201201168Citations: 6Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Reading the tea leaves: The enatioselective total syntheses of 8-C-ascorbyl-(−)-epigallocatechin was accomplished by CuII-mediated oxidative coupling of ascorbic acid and (−)-epigallocatechin as a key step. Also, the asymmetric total syntheses of tea-leaf extracts (+)-gallocatechin and (−)-epigallocatechin were achieved by Au-catalyzed intramolecular cycliarylation of the precursor epoxide and Sharpless dihydroxylation. Citing Literature Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description asia_201201168_sm_miscellaneous_information.pdf1.3 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume8, Issue4April 2013Pages 700-704 RelatedInformation