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

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 BF ·Et O. Subseque...

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Veröffentlicht in:Organic & biomolecular chemistry 2017, Vol.15 (23), p.5025-5032
Hauptverfasser: Arai, Midori A, Yamaguchi, Yumi, Ishibashi, Masami
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Sprache:eng
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Zusammenfassung: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 BF ·Et O. 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01004d