Stereoselective synthesis of cis-2,5-disubstituted THFs: application to adjacent bis-THF cores of Annonaceous acetogenins.

@article{Fujioka2012StereoselectiveSO,
  title={Stereoselective synthesis of cis-2,5-disubstituted THFs: application to adjacent bis-THF cores of Annonaceous acetogenins.},
  author={H. Fujioka and Ryota Maehata and Shintaro Wakamatsu and Kenji Nakahara and Tatsuya Hayashi and Tomohiro Oki},
  journal={Organic letters},
  year={2012},
  volume={14 4},
  pages={
          1054-7
        }
}
The iodocyclization of γ,δ-unsaturated alcohols in the presence of a silyl enol ether produced cis-2,5-disubstituted tetrahydrofurans in one pot via siloxy intermediates. N-Iodosuccinimide (NIS) effectively worked as an activator of the double bonds in the substrates and the silyl enol ether. Application to an expedient synthesis of the adjacent bis-tetrahydrofuran core of Annonaceous acetogenins with a cis/threo/cis relative stereochemistry is also described. 
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