Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity.

@article{Kodanko2007SynthesisOA,
  title={Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity.},
  author={Jeremy J Kodanko and S. Hiebert and E. Peterson and Leonard Sung and L. E. Overman and Viviane de Moura Linck and Greice Catrine Goerck and T. A. Amador and M. Leal and E. Elisabetsky},
  journal={The Journal of organic chemistry},
  year={2007},
  volume={72 21},
  pages={
          7909-14
        }
}
  • Jeremy J Kodanko, S. Hiebert, +7 authors E. Elisabetsky
  • Published 2007
  • Chemistry, Medicine
  • The Journal of organic chemistry
  • The previously unknown stereoisomers 3, 4, ent-1, and ent-4 of the tris(pyrrolidinoindoline) alkaloids hodgkinsine (1) and hodgkinsine B (2) were prepared by stereocontrolled total synthesis. In each synthesis, a catalyst-controlled intramolecular Heck reaction was the key step in appending a third cis-pyrrolidinoindoline ring to a hexacyclic chimonanthine precursor. Results of the preliminary evaluation of these hodgkinsine stereoisomers in the tail flick and capsaicin pain models are reported… CONTINUE READING
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