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 |
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Format: | Artikel |
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. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c7ob01004d |