Convergent Diastereoselective Synthesis of Isopilocarpine by One-Pot Michael-Addition-Alkylation Reaction

@article{Braun2004ConvergentDS,
  title={Convergent Diastereoselective Synthesis of Isopilocarpine by One-Pot Michael-Addition-Alkylation Reaction},
  author={Manfred Braun and Corinna B{\"u}hne and Dimitrula Cougali and Klaus-J. Schaper and Walter Frank},
  journal={Synthesis},
  year={2004},
  volume={2004},
  pages={2905-2909}
}
The metalated dithiane 7b available from imidazole aldehyde 6 is reacted with furanone 4 and ethyl iodide to give the lactone 8, which forms diastereoselectively. Its configuration is determined to be trans by means of a crystal structure analysis. The desulfurization of 8 leads to the alkaloid isopilocarpine 2 in three steps and 25% overall yield. The relative energies of the diastereo meric alkaloids 1 and 2 have been calculated. 

Figures from this paper

Imidazole, oxazole and thiazole alkaloids.

  • Zhong Jin
  • Chemistry, Biology
    Natural product reports
  • 2006
TLDR
This review, with 186 references cited, gives an account of the chemistry and biology of these biologically significant secondary metabolites of terrestrial and marine microorganisms as well as marine invertebrates.

Unraveling the Biosynthesis of Pilocarpine in Pilocarpus microphyllus

TLDR
A biosynthesis pathway for pilocarpine is suggested and further experiments using labeled precursors associated with transcriptome data may allow to understand the whole biosynthetic pathway and its genetic control.

Intermolecular interactions between cucurbit[7]uril and pilocarpine.

References

SHOWING 1-4 OF 4 REFERENCES

SHELXS86, Program for the Solution of Crystal Structures

  • University of Göttingen: Germany,
  • 1985

Recl

  • J . R . Neth . Chem . Soc .
  • 1979

SHELXL97, Program for the Refinement of Crystal Structures

  • University of Göttingen: Germany,
  • 1997