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

Midori A. Arai, Yumi Yamaguchi, Masami Ishibashi

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5025-5032
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number23
DOIs
Publication statusPublished - 2017 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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