Total synthesis of vineomycin B2

Shunichi Kusumi, Satoshi Tomono, Shunsuke Okuzawa, Erika Kaneko, Takashi Ueda, Kaname Sasaki, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The first total synthesis of vineomycin B2 (1) has been accomplished. The aglycon segment, a vineomycinone B2 derivative, and the glycon segment, an α-l-acurosyl-l-rhodinose derivative, were prepared via C-glycosylation using an unprotected sugar and powerful chemoselective O-glycosylation using a 2,3-unsaturated sugar, respectively, as the key steps. Furthermore, effective and simultaneous introduction of the two glycon moieties to the aglycon part by concentration-controlled glycosylation led to the total synthesis of 1.

Original languageEnglish
Pages (from-to)15909-15912
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number42
DOIs
Publication statusPublished - 2013 Jan 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Kusumi, S., Tomono, S., Okuzawa, S., Kaneko, E., Ueda, T., Sasaki, K., Takahashi, D., & Toshima, K. (2013). Total synthesis of vineomycin B2. Journal of the American Chemical Society, 135(42), 15909-15912. https://doi.org/10.1021/ja407827n