Synthesis of PDE IVb Inhibitors. 3. Synthesis of (+)-, (-)-, and (±)-7-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one via reductive domino transformations of 3-β-carbomethoxyethyl-substituted six-membered cyclic nitronates.

@article{Sukhorukov2012SynthesisOP,
  title={Synthesis of PDE IVb Inhibitors. 3. Synthesis of (+)-, (-)-, and (±)-7-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one via reductive domino transformations of 3-$\beta$-carbomethoxyethyl-substituted six-membered cyclic nitronates.},
  author={A. Sukhorukov and Yaroslav D Boyko and Y. Nelyubina and St{\'e}phane G{\'e}rard and S. Ioffe and V. A. Tartakovsky and Laurette Laurette Malleret and A. Belaaouaj},
  journal={The Journal of organic chemistry},
  year={2012},
  volume={77 12},
  pages={
          5465-9
        }
}
Simple three-step asymmetric and racemic syntheses of GlaxoSmithKline's highly potent PDE IVb inhibitor 1 were developed. The suggested approach is based on reductive domino transformations of 3-β-carbomethoxyethyl-substituted six-membered cyclic nitronates, which are easily accessed by a stereoselective [4 + 2] cycloaddition of an appropriate nitroalkene to vinyl ethers. In vitro studies of PDE IVb inhibition by enantiomeric pyrrolizidinones (+)-1 and (-)-1 were performed. 
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References

SHOWING 1-10 OF 15 REFERENCES
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