Photooxygenation of a microbial arene oxidation product and regioselective Kornblum-DeLaMare rearrangement: total synthesis of zeylenols and zeylenones.
Photooxygenation of a microbial arene oxidation product and regioselective Kornblum-DeLaMare rearrangement: total synthesis of zeylenols and zeylenones.
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DOI：
10.1002/chem.201104035
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发表时间：
2012-04
期刊：
影响因子：
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通讯作者：
M. Palframan;G. Kociok‐Köhn;S. Lewis
中科院分区：
文献类型：
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作者：
M. Palframan;G. Kociok‐Köhn;S. Lewis
报道了Zeylenol（+）-1及其同系物（-）-7和16以及3-O-脱苯甲酰Zeylenone 28的对映选择性全合成。为此，Kornblum-DeLaMare重排，利用相邻基团的参与，赋予区域选择性的一个新的变种，已经开发出来。该方法采用源自微生物芳烃氧化产物的结构单元的光氧化。
We report the enantioselective total syntheses of zeylenol (+)-1, as well as its congeners (-)-7 and 16, and of 3-O-debenzoylzeylenone 28. To this end, a new variant of the Kornblum-DeLaMare rearrangement, which utilises neighbouring-group participation to impart regioselectivity, has been developed. The approach employs photooxygenation of building blocks derived from a microbial arene oxidation product.