Total Synthesis of Aquayamycin
Total Synthesis of Aquayamycin
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DOI：
10.1002/chem.201604697
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发表时间：
2016-12-23
影响因子：
4.3
通讯作者：
Toshima, Kazunobu
中科院分区：
文献类型：
--
作者：
Kusumi, Shunichi;Nakayama, Harunobu;Toshima, Kazunobu
实现了一种高效实用的水霉素全合成方法。通过三个关键反应构建了高度氧化和立体化学复杂的四环体系：1）C-糖基萘基锂与环酮的高度非对映选择性1，2-加成，2）铟介导的萘醌的位点选择性烯丙基化-重排序列，3）非对映选择性分子内频哪醇偶联.该合成策略为水霉素型安卡环素类抗生素的合成提供了一条新的有效途径。
An efficient and practical total synthesis of aquayamycin has been accomplished. The highly oxidized and stereochemically complex tetracyclic ring system was constructed using three key reactions: 1) highly diastereo-selective 1,2-addition of C-glycosyl naphthyllithium to a cyclic ketone, 2) indium-mediated site-selective allylation-rearrangement sequence of naphthoquinone, and 3) diastereoselective intramolecular pinacol coupling. This synthetic strategy offers a novel and efficient pathway to prepare aquayamycin-type angucycline antibiotics.