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).

Nagarjuna Reddy Guttikonda, Rama Mohana Reddy Jaggavarapu, Muvvala Venkatanarayana, Raja Reddy Kamatham, Akula Nagarjuna, Ravi Kumar Cheedarala, Ravikumar Surepally

Current organic synthesis 2023

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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. 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. The intramolecular isomerization process was successfully applied for the separation of enantio-pure isomers with no impurities using DBU. The chemical structures of A-MP and B-MP were confirmed using spectral analyses of 1H-NMR, 13C-NMR and Mass spectroscopy. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.

Citation

Nagarjuna Reddy Guttikonda, Rama Mohana Reddy Jaggavarapu, Muvvala Venkatanarayana, Raja Reddy Kamatham, Akula Nagarjuna, Ravi Kumar Cheedarala, Ravikumar Surepally. 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). Current organic synthesis. 2023;20(4):484-490