Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules.

@article{Sundn2010AsymmetricSO,
  title={Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules.},
  author={Henrik Sund{\'e}n and Roger Olsson},
  journal={Organic & biomolecular chemistry},
  year={2010},
  volume={8 21},
  pages={
          4831-3
        }
}
An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C catalyzed reduction yields the target molecule in 21% overall yield over 6 steps. 

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