Total Synthesis of Vineomycin B2

被引：26

作者：

Kusumi, Shunichi ^{[1
]}

Tomono, Satoshi ^{[1
]}

Okuzawa, Shunsuke ^{[1
]}

Kaneko, Erika ^{[1
]}

Ueda, Takashi ^{[1
]}

Sasaki, Kaname ^{[1
]}

Takahashi, Daisuke ^{[1
]}

Toshima, Kazunobu ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 42期

关键词：

C-ARYLGLYCOSYLATION; METHYL-ESTER; GLYCOSYLATION; ARYL; LACTONAMYCIN; GLYCOSIDES; STRATEGY;

D O I：

10.1021/ja407827n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of vineomycin B-2 (1) has been accomplished. The aglycon segment, a vineomycinone B-2 derivative, and the glycon segment, an alpha-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.

引用

页码：15909 / 15912

页数：4

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