Toward the total synthesis of vineomycin B2: application of an efficient glycosylation methodology using 2,3-unsaturated sugars

Kaname Sasaki, Shuichi Matsumura, Kazunobu Toshima

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The application of an efficient glycosylation methodology using 2,3-unsaturated sugars to synthesize critical precursors required for the total synthesis of an antibiotic, vineomycin B2 (1), was demonstrated. The required disaccharide, the acurosyl rhodinose derivative of 1, was prepared by chemoselective glycosylation using a 2,3-saturated glycosyl acetate corresponding to the rhodinose moiety and a 2,3-unsaturated glycosyl acetate corresponding to the acurose portion. Further, the right-hand side chain of 1, consisting of β-oxo-tert-alcohol and rhodinose, was constructed by a powerful glycosylation approach using a 2,3-unsaturated glycosyl acetate in an ionic liquid under reduced pressure.

Original languageEnglish
Pages (from-to)6982-6986
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number39
DOIs
Publication statusPublished - 2007 Sep 24

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Glycosylation
Sugars
Acetates
Ionic Liquids
Disaccharides
Alcohols
Anti-Bacterial Agents
Derivatives
Pressure
vineomycin B2
rhodinose

Keywords

  • 2,3-Unsaturated sugar
  • Chemoselectivity
  • Glycosylation
  • Ionic liquid
  • Vineomycin B

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Toward the total synthesis of vineomycin B2 : application of an efficient glycosylation methodology using 2,3-unsaturated sugars. / Sasaki, Kaname; Matsumura, Shuichi; Toshima, Kazunobu.

In: Tetrahedron Letters, Vol. 48, No. 39, 24.09.2007, p. 6982-6986.

Research output: Contribution to journalArticle

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