Total Synthesis of Terpioside B

Kazuki Inaba, Masato Endo, Naoto Iibuchi, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticle

Abstract

The first total synthesis of terpioside B (1) has been accomplished. Key steps include the stereoselective installments of a set of challenging 1,2-cis-glycosidic linkages. Thus, α(1,4)-linked d-galactoside was effectively constructed from a 1,2-anhydrogalactose donor and an unprotected 1,6-anhydrogalactose acceptor by using a boron-mediated aglycon delivery (BMAD) method. In addition, α-l-fucofuranosides were stereoselectively and simultaneously constructed by remote group-assisted 1,2-cis-α-stereoselective glycosylations.

Original languageEnglish
Pages (from-to)10222-10225
Number of pages4
JournalChemistry - A European Journal
Volume26
Issue number45
DOIs
Publication statusPublished - 2020 Aug 12

Keywords

  • boron-mediated aglycon delivery
  • glycosphingolipids
  • glycosylation
  • terpioside B
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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