Synthetic approaches to brevianamides A and B I. Preparation of 4-p-methoxybenzyl-5-(1′-carbomethoxy-2′-[1″, 1″-dimethylallyl-2′, 3′dihydroindole]methylidene)-1, 2-L-pyrolidinopiperazine-3, 6-dione via an Ireland ester enolate claisen rearrangement.

@article{Dunkerton1988SyntheticAT,
  title={Synthetic approaches to brevianamides A and B I. Preparation of 4-p-methoxybenzyl-5-(1′-carbomethoxy-2′-[1″, 1″-dimethylallyl-2′, 3′dihydroindole]methylidene)-1, 2-L-pyrolidinopiperazine-3, 6-dione via an Ireland ester enolate claisen rearrangement.},
  author={L. Dunkerton and H. Chen and B. P. Mckillican},
  journal={Tetrahedron Letters},
  year={1988},
  volume={29},
  pages={2539-2542}
}
Abstract Using an ester enolate Claisen rearrangement to prepare 1-carbomethoxy-2-(1′, 1′-dimethylallyl)-2, 3-dihydroindole-2-carboxylic acid followed by condensation with N-p-methoxybenzyl-glycyl-L-proline anhydride gave the title compound, a key intermediate in a synthetic approach to brevianamides A and B. 
14 Citations
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