Issue 23, 2017
From the journal:

Organic & Biomolecular Chemistry

Total synthesis of agalloside, isolated from Aquilaria agallocha, by the 5-O-glycosylation of flavan†

Midori A. Arai, ORCID logo *a   Yumi Yamaguchia  and  Masami Ishibashi ORCID logo *a  

* Corresponding authors

a Department of Natural Product Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, Japan
E-mail: midori_arai@chiba-u.jp, mish@chiba-u.jp

Abstract

Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.

Graphical abstract: Total synthesis of agalloside, isolated from Aquilaria agallocha, by the 5-O-glycosylation of flavan

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Article information

DOI
https://doi.org/10.1039/C7OB01004D
Article type
Paper
Submitted
25 Apr 2017
Accepted
20 May 2017
First published
01 Jun 2017

Org. Biomol. Chem., 2017,15, 5025-5032

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Total synthesis of agalloside, isolated from Aquilaria agallocha, by the 5-O-glycosylation of flavan

M. A. Arai, Y. Yamaguchi and M. Ishibashi, Org. Biomol. Chem., 2017, 15, 5025 DOI: 10.1039/C7OB01004D

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