Efficient synthesis of monoacyl dipyrromethanes and their use in the preparation of sterically unhindered trans-porphyrins.

@article{Rao2000EfficientSO,
  title={Efficient synthesis of monoacyl dipyrromethanes and their use in the preparation of sterically unhindered trans-porphyrins.},
  author={Pinzeng Rao and Benjamin J. Littler and G R Geier and Jonathan S. Lindsey},
  journal={The Journal of organic chemistry},
  year={2000},
  volume={65 4},
  pages={1084-92}
}
The condensation of an aldehyde with a dipyrromethane bearing a sterically unhindered aryl substituent at the 5-position typically results in low yield and a mixture of porphyrin products derived from acidolytic scrambling. We have developed a concise nonscrambling synthesis of such trans-porphyrins that takes advantage of the availability of multigram quantities of dipyrromethanes. This route involves the selective monoacylation of the dipyrromethanes with a pyridyl thioester, reduction of the… CONTINUE READING