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

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Glycosylation
Sugars
Derivatives
vineomycin B2

ASJC Scopus subject areas

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

Cite this

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

Total synthesis of vineomycin B2. / Kusumi, Shunichi; Tomono, Satoshi; Okuzawa, Shunsuke; Kaneko, Erika; Ueda, Takashi; Sasaki, Kaname; Takahashi, Daisuke; Toshima, Kazunobu.

In: Journal of the American Chemical Society, Vol. 135, No. 42, 2013, p. 15909-15912.

Research output: Contribution to journalArticle

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, vol. 135, no. 42, pp. 15909-15912. https://doi.org/10.1021/ja407827n
Kusumi S, Tomono S, Okuzawa S, Kaneko E, Ueda T, Sasaki K et al. Total synthesis of vineomycin B2. Journal of the American Chemical Society. 2013;135(42):15909-15912. https://doi.org/10.1021/ja407827n
Kusumi, Shunichi ; Tomono, Satoshi ; Okuzawa, Shunsuke ; Kaneko, Erika ; Ueda, Takashi ; Sasaki, Kaname ; Takahashi, Daisuke ; Toshima, Kazunobu. / Total synthesis of vineomycin B2. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 42. pp. 15909-15912.
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