Intramolecular oxonium ylide formation-[2,3] sigmatropic rearrangement of diazocarbonyl-substituted cyclic unsaturated acetals: a formal synthesis of hyperolactone C.

@article{Hodgson2014IntramolecularOY,
  title={Intramolecular oxonium ylide formation-[2,3] sigmatropic rearrangement of diazocarbonyl-substituted cyclic unsaturated acetals: a formal synthesis of hyperolactone C.},
  author={D. Hodgson and S. Man and Kimberley J. Powell and Ziga Perko and Minxiang Zeng and Elena Moreno-Clavijo and A. Thompson and M. D. Moore},
  journal={The Journal of organic chemistry},
  year={2014},
  volume={79 20},
  pages={
          9728-34
        }
}
  • D. Hodgson, S. Man, +5 authors M. D. Moore
  • Published 2014
  • Chemistry, Medicine
  • The Journal of organic chemistry
  • Rh(II)-catalyzed oxonium ylide formation-[2,3] sigmatropic rearrangement of α-diazo-β-ketoesters possessing γ-cyclic unsaturated acetal substitution, followed by acid-catalyzed elimination-lactonization, provides a concise approach to 1,7-dioxaspiro[4.4]non-2-ene-4,6-diones. The process creates adjacent quaternary stereocenters with full control of the relative stereochemistry. An unsymmetrical monomethylated cyclic unsaturated acetal leads to hyperolactone C, where ylide formation… CONTINUE READING
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