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)

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.