Repraesentin F 的全合成及通过金（I）催化的环化级联反应进行的构型重排
Total Synthesis of Repraesentin F and Configuration Reassignment by a Gold(I)-Catalyzed Cyclization Cascade.
机构信息
Institute of Chemical Research of Catalonia (ICIQ) , Barcelona Institute of Science and Technology , Av. Països Catalans 16 , 43007 Tarragona , Spain.
Departament de Química Analítica i Química Orgànica , Universitat Rovira i Virgili , C/Marcel·lí Domingo s/n , 43007 Tarragona , Spain.
出版信息
Org Lett. 2018 Sep 21;20(18):5784-5788. doi: 10.1021/acs.orglett.8b02478. Epub 2018 Sep 10.
The first total synthesis of repraesentin F has been accomplished by a highly diastereoselective gold(I)-catalyzed cyclization cascade as the key step. This cycloisomerization/Prins-type tandem transformation enabled direct access to the atypical tricyclic carbon skeleton of the natural product with the required syn/ anti/ syn ring fusion. This synthetic effort also allowed reassignment of the relative configuration of repraesentin F and determination of its absolute configuration.
首次通过高度非对映选择性的金（I）催化环化级联反应完成了 repraesentin F 的全合成，该反应是关键步骤。这种环异构化/Prins 型串联转化反应可以直接构建天然产物中具有所需 syn/anti/syn 环稠合的非典型三环碳骨架。这一合成努力还允许重新分配 repraesentin F 的相对构型并确定其绝对构型。
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