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

Authors :
Midori A. Arai
Yumi Yamaguchi
Masami Ishibashi
Source :
Organic & Biomolecular Chemistry. 15:5025-5032
Publication Year :
2017
Publisher :
Royal Society of Chemistry (RSC), 2017.

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.

Details

ISSN :
14770539 and 14770520
Volume :
15
Database :
OpenAIRE
Journal :
Organic & Biomolecular Chemistry
Accession number :
edsair.doi.dedup.....c836e5f697173c3de8f850e0e6171465
Full Text :
https://doi.org/10.1039/c7ob01004d