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

Midori A. Arai, Yumi Yamaguchi, Masami Ishibashi

研究成果: Article査読

9 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)5025-5032
ページ数8
ジャーナルOrganic and Biomolecular Chemistry
15
23
DOI
出版ステータスPublished - 2017
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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