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Enantioselective syntheses of the proposed structures of kopeolin and kopeolone

机译:对映体的合成的kopeolin和kopeolone拟议的结构

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The first total syntheses of the proposed structures of kopeolin (1) and kopeolone (3) have been achieved from a common enantiopure chiral building block obtained by a chemoenzymatic enantioconvergent methodology. The syntheses feature two key steps: a one-pot reduction/diastereoselective protonation followed by a highly diastereoselective addition of an organocerate. The synthetic structures were fully characterized and all stereocenters were confirmed. The results show that the two previously reported structures were not assigned correctly, and suggest an initial structural misassignment during the isolation of the natural products. Thus, two revised structures, 1′ for kopeolin and 3′ for kopeolone, are proposed.
机译:拟议的kopeolin(1)和kopeolone(3)结构的第一个总合成是通过化学酶对映体收敛方法获得的常见对映纯手性结构单元实现的。合成具有两个关键步骤:一锅还原/非对映选择性质子化,然后高度非对映选择性地添加有机铈酸盐。对合成结构进行了充分表征,并确定了所有立体中心。结果表明,先前报道的两个结构分配不正确,并且表明在天然产物的分离过程中存在初始结构错配。因此,提出了两个修改的结构,即针对高peolin的1'和针对kopeolone的3'。

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