The Synthesis of Melohenine B and a Related Natural Product
The Synthesis of Melohenine B and a Related Natural Product
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DOI：
10.1021/ol302859j
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发表时间：
2012-12-21
期刊：
影响因子：
5.2
通讯作者：
Westwood, Nicholas J.
中科院分区：
文献类型：
--
作者：
Lancefield, Christopher S.;Zhou, Linna;Westwood, Nicholas J.
以依勃那敏为原料，通过仿生非对映选择性单线态氧介导的吲哚C2-C7键的氧化断裂，合成了美洛海宁B和O-乙基-14-表美洛海宁B。这些研究使天然产物的绝对构型的分配。根据提出的生物合成途径，所得的含九元环的产物可以转化为相应的喹诺酮。
A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.