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Synthetic Efforts toward the Spiroketal Core of Spirangien A

  作者 GUERINOT AMANDINE; LEPESQUEUX GUILLAUME; SABLE SERGE; REYMOND SEBASTIEN; COSSY JANINE  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-15;  页码  5151-5163  
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[摘要]Synthetic studies toward the spiroketal core of spirangien A are described. Two synthetic approaches were developed. Both of them use a diastereoselective aldol addition of a lithium enolate derived from a methyl ketone on an aldehyde. In the first approach, the introduction of the (E)-trisubstituted terminal olefin was achieved by using an iron-catalyzed cross-coupling between an alkyl iodide and a vinyl Grignard reagent and a randomly protected spiroketal was obtained. In the second approach, a highly functionalized spiroketal carbamate, which includes 13 stereogenic centers, was successfully isolated.

 
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