Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement.

@article{Hodgson2011SynthesisOT,
  title={Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement.},
  author={D. Hodgson and S. Man},
  journal={Chemistry},
  year={2011},
  volume={17 35},
  pages={
          9731-7
        }
}
  • D. Hodgson, S. Man
  • Published 2011
  • Chemistry, Medicine
  • Chemistry
  • Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled Rh(II) -catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an α-diazo-β-ketoester bearing allylic ether functionality. From the resulting furanone, an acid-catalysed lactonisation and dehydrogenation gives the natural product… CONTINUE READING
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