Synthesis of Misoprostol, and Intramolecular Isomerization of A-Type Misoprostol into B-Type Misoprostol using 1, 8-Diazabicyclo [5.4.0] undec- 7-ene (DBU)

Curr Org Synth. 2023;20(4):484-490. doi: 10.2174/1570179419666220831100708.

Abstract

Objective: Misoprostol is a synthetic prostaglandin that is related structurally to naturally occurring prostaglandin (PG), and it has been acknowledged as an effective inhibitor of gastric acid secretion when administered intravenously.

Methods: In the present study, the novel application of 1,8-Diazabicyclo[5.4.0]undec-7-ene, a cyclic unsaturated amine [DBU] for the conversion of A-type Misoprostol (A-MP) to B-type Misoprostol (B-MP) via intramolecular isomerization.

Results: The intramolecular isomerization process was successfully applied for the separation of enantio-pure isomers with no impurities using DBU.

Conclusion: The chemical structures of A-MP and B-MP were confirmed using spectral analyses of 1H-NMR, 13C-NMR and Mass spectroscopy.

Keywords: DBU; Misoprostol; inhibitor; intra molecular; isomerization; prostaglandin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Isomerism
  • Misoprostol*
  • Prostaglandins, Synthetic

Substances

  • Misoprostol
  • Prostaglandins, Synthetic