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Synthesis of Misoprostol, and Intramolecular Isomerization of A-Type Misoprostol into B-Type Misoprostol using 1,
Nagarjuna Reddy Guttikonda1, Rama Mohana Reddy Jaggavarapu1, Muvvala Venkatanarayana1
1Department of Chemistry, GITAM (Deemed to be University), Hyderabad, Telangana-502329, India.
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.
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