Synthesis and assignment of absolute configuration of the iridoid 9-deoxygelsemide.

@article{Dalfonso2010SynthesisAA,
  title={Synthesis and assignment of absolute configuration of the iridoid 9-deoxygelsemide.},
  author={Alessandro D'alfonso and Maurizio Pasi and Alessio Porta and Giuseppe Zanoni and Giovanni Vidari},
  journal={Organic letters},
  year={2010},
  volume={12 3},
  pages={
          596-9
        }
}
The first enantioselective synthesis of 9-deoxygelsemide, belonging to a rare group of iridoids isolated from Gelsemium plants, is described. The key synthetic steps are a variant of the Woodward-Prevost reaction to install the characteristic cis-alpha-1,2-dioxygenated system at C-6 and C-7 with complete diastereoselectivity. Construction of the dihydropyran ring was achieved via formylation of lactone I, followed by dehydration of the corresponding lactol. The synthesis allowed assignment of… Expand
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