The Stille reaction in the synthesis of the C37-norcarotenoid butenolide pyrrhoxanthin. Scope and limitations.

@article{Vaz2006TheSR,
  title={The Stille reaction in the synthesis of the C37-norcarotenoid butenolide pyrrhoxanthin. Scope and limitations.},
  author={Belén Vaz and M. Dom{\'i}nguez and R. {\'A}lvarez and {\'A}. D. de Lera},
  journal={The Journal of organic chemistry},
  year={2006},
  volume={71 16},
  pages={
          5914-20
        }
}
The sequential Stille cross-coupling reactions of the dihalogenated gamma-alkylidenebutenolide 7 with stannanes 9 and 6 afforded the carbon skeleton of pyrrhoxanthin, a highly functionalized C7'-C8' acetylenic C37-norcarotenoid butenolide. Although the first halogen-selective Stille coupling takes place in 90% yield at ambient temperature, double isomerization of the Z,E- to the E,Z-C7'-C10' enyne, likely induced by the catalyst, accompanyied the bond formation, leading to 9'Z-20 and… Expand
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