Issue 10, 2013
From the journal:

Chemical Science

Synthetic access toward the diverse ginsenosides†

Jun Yu,ab   Jiansong Sun,*a   Yiming Niu,c   Rongyao Li,c   Jinxi Liao,b   Fuyi Zhangc  and  Biao Yu*a  

* Corresponding authors

a State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: jssun@mail.sioc.ac.cn, byu@mail.sioc.ac.cn
Fax: +86-21-64166128

b Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China

c Department of Chemistry, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China

Abstract

All the possible types of the protopanaxatriol and protopanaxadiol glycosides, the major active yet extremely heterogeneous principles of ginsengs, could be accessed by the present sequence of transformations, including global removal of the sugar residues from the crude ginseng extracts and stepwise elaboration of the glycans onto the aglycone. In particular, intramolecular hydrogen-bonding and neutral conditions have enabled glycosylation of the highly sterically hindered and acid labile dammarane C20-OH.

Graphical abstract: Synthetic access toward the diverse ginsenosides

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Article information

DOI
https://doi.org/10.1039/C3SC51479J
Article type
Edge Article
Submitted
26 May 2013
Accepted
22 Jul 2013
First published
24 Jul 2013

Chem. Sci., 2013,4, 3899-3905

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Synthetic access toward the diverse ginsenosides

J. Yu, J. Sun, Y. Niu, R. Li, J. Liao, F. Zhang and B. Yu, Chem. Sci., 2013, 4, 3899 DOI: 10.1039/C3SC51479J

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