Ketyl radical cyclization of β-disubstituted acrylates: formal syntheses of (+)-secosyrin 1 and longianone and the total synthesis of (+)-4-epi-secosyrin 1.

@article{Donner2013KetylRC,
  title={Ketyl radical cyclization of β-disubstituted acrylates: formal syntheses of (+)-secosyrin 1 and longianone and the total synthesis of (+)-4-epi-secosyrin 1.},
  author={C. Donner},
  journal={Organic letters},
  year={2013},
  volume={15 6},
  pages={
          1258-61
        }
}
  • C. Donner
  • Published 2013
  • Chemistry, Medicine
  • Organic letters
  • A novel approach to the synthesis of a series of 1,7-dioxaspirononanes that applies a ketyl radical cyclization strategy is described. Radical cyclization of the β-disubstituted acrylate 23, prepared in five steps from (R)-1,2-isopropylideneglycerol, gives both 2,3-syn- and 2,3-anti-furan products. The densely functionalized furan heterocycles are used to complete a concise formal synthesis of secosyrin 1, a metabolite of Pseudomonas syringae, and the total synthesis of 4-epi-secosyrin 1. 
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