Total Synthesis of Vineomycin B2

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• 作者：Shunichi Kusumi ; Satoshi Tomono ; Shunsuke Okuzawa ; Erika Kaneko ; Takashi Ueda ; Kaname Sasaki ; Daisuke Takahashi ; Kazunobu Toshima
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：October 23, 2013
• 年：2013
• 卷：135
• 期：42
• 页码：15909-15912
• 全文大小：289K
• 年卷期：v.135,no.42(October 23, 2013)
• ISSN：1520-5126

文摘

The first total synthesis of vineomycin B₂ (1) has been accomplished. The aglycon segment, a vineomycinone B₂ derivative, and the glycon segment, an 伪-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.