%0 Journal Article %A Guérinot, Amandine %A Lepesqueux, Guillaume %A Sablé, Serge %A Reymond, Sébastien %A Cossy, Janine %D 2010 %T Synthetic Efforts toward the Spiroketal Core of Spirangien A %U https://acs.figshare.com/articles/journal_contribution/Synthetic_Efforts_toward_the_Spiroketal_Core_of_Spirangien_A/2744755 %R 10.1021/jo100871m.s001 %2 https://ndownloader.figshare.com/files/4423300 %K diastereoselective aldol addition %K spiroketal core %K methyl ketone %K Spirangien ASynthetic studies %K approach %K alkyl iodide %K 13 stereogenic centers %K functionalized spiroketal carbamate %K Synthetic Efforts %K vinyl Grignard reagent %K lithium enolate %K Spiroketal Core %X 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. %I ACS Publications