Short, Enantioselective Total Syntheses of Fugomycin and Desoxyfugomycin via Sonogashira Alkynylation of α-Bromobutenolides

@article{Boukouvalas2013ShortET,
  title={Short, Enantioselective Total Syntheses of Fugomycin and Desoxyfugomycin via Sonogashira Alkynylation of $\alpha$-Bromobutenolides},
  author={John Boukouvalas and Nicolas Bruneau-Latour},
  journal={Synlett},
  year={2013},
  volume={24},
  pages={2691-2694}
}
The potent antifungal antibiotics (+)-fugomycin and (+)-desoxyfugomycin were synthesized in 3–4 steps with high overall efficiency (51–53%) and optical purity (ee > 97%). The syntheses illustrate a highly effective protocol for accomplishing racemization-free Sonogashira coupling of chiral α-bromobutenolides, and the usefulness of the Movassaghi–Jacobsen method for preparing the latter from epoxides. 
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