Facile formation of tetrahydrofurans with multiple chiral centers using double iodoetherification of σ-symmetric diene acetals : short asymmetric total synthesis of rubrenolide and rubrynolide

@article{Fujioka2008FacileFO,
  title={Facile formation of tetrahydrofurans with multiple chiral centers using double iodoetherification of $\sigma$-symmetric diene acetals : short asymmetric total synthesis of rubrenolide and rubrynolide},
  author={H. Fujioka and Yusuke Ohba and Hideki Hirose and Kenji Nakahara and Kenichi Murai and Y. Kita},
  journal={Tetrahedron},
  year={2008},
  volume={64},
  pages={4233-4245}
}
Abstract A novel double intramolecular iodoetherification of σ-symmetric diene acetals from (R,R)-hydrobenzoin occurred in highly diastereoselective manners to give tetrahydrofuran moieties with multiple chiral centers in a one-pot operation. The chemoselective discrimination of the two iodomethyl functions in the products was attained in various reactions. The reaction was applied to the concise asymmetric syntheses of rubrenolide and rubrynolide, in which the unit from the chiral auxiliary… Expand
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References

SHOWING 1-10 OF 32 REFERENCES
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1
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3
4
...