Enantiospecific Synthesis of (R)-4-Amino-5-oxo-1,3,4,5-tetrahydrobenz[cd]indole, an Advanced Intermediate Containing the Tricyclic Core of the Ergots.

@article{Hurt1999EnantiospecificSO,
  title={Enantiospecific Synthesis of (R)-4-Amino-5-oxo-1,3,4,5-tetrahydrobenz[cd]indole, an Advanced Intermediate Containing the Tricyclic Core of the Ergots.},
  author={Clarence R. Hurt and Ronghui Lin and Henry Rapoport},
  journal={The Journal of organic chemistry},
  year={1999},
  volume={64 1},
  pages={225-233}
}
We report a new strategy for the enantiospecific synthesis of (R)-4-amino-5-oxo-1,3,4,5-tetrahydrobenz[cd]indole. This compound is an advanced intermediate which contains the tricyclic core of many of the tetracyclic ergot alkaloids. Our method involves the initial synthesis of D-4-bromotryptophan from the coupling of an indolyllithium species with a masked serinal. The alpha-amino position was protected with an N-trityl group, ensuring the enantiomeric integrity of this position during the… CONTINUE READING