Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone.

@article{Feldman2002AlkynyliodoniumSI,
  title={Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone.},
  author={K. Feldman and Timothy D. Cutarelli},
  journal={Journal of the American Chemical Society},
  year={2002},
  volume={124 39},
  pages={
          11600-1
        }
}
  • K. Feldman, Timothy D. Cutarelli
  • Published 2002
  • Chemistry, Medicine
  • Journal of the American Chemical Society
  • The synthesis of the tropoloisoquinoline alkaloid pareitropone has been accomplished in 14 steps from 2,3,4-trimethoxybenzoic acid. The key transformations include the generation of an alkylidenecarbene intermediate through intramolecular addition of a tosylamide anion to an alkynyliodonium salt, and the cycloaddition of that carbene to a peri positioned aromatic ring to afford a cycloheptatrienylidene product featuring the intact pareitropone skeleton. 
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