Total synthesis and structure revision of deacetylravidomycin M
Total synthesis and structure revision of deacetylravidomycin M
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DOI：
10.1016/j.tet.2011.06.046
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发表时间：
2011-09-02
期刊：
影响因子：
2.1
通讯作者：
Suzuki, Keisuke
中科院分区：
文献类型：
--
作者：
Ben, Akimi;Hsu, Day-Shin;Suzuki, Keisuke
完成了脱乙酰拉维霉素 M 非天然对映体的全合成。关键步骤包括：（1）使用催化Sc（OTf）（3）对带有叠氮基的岩藻糖基乙酸酯2进行芳基C-糖苷化，（2）带有叠氮基糖的烷氧基苯炔与烯酮甲硅烷基缩醛的[2+2]环加成反应，以及（3）烷氧基苯并环丁烯酮的扩环反应。合成表明天然产物不是所提出的胺，而是相应的N-氧化物。 (C) 2011 Elsevier Ltd. 保留所有权利。
Total synthesis of the unnatural enantiomer of deacetylravidomycin M was accomplished. The key steps include, (1) aryl C-glycosidation of the azido-bearing fucosyl acetate 2 by using catalytic Sc(OTf)(3), (2) the [2+2] cycloaddition reaction of alkoxybenzyne bearing an azido sugar to ketene silyl acetal, and (3) the ring expansion reaction of alkoxybenzocyclobutenone. The synthesis revealed that the natural product is not the proposed amine, but the corresponding N-oxide. (C) 2011 Elsevier Ltd. All rights reserved.