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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

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)

Author(s): Nagarjuna Reddy Guttikonda, Rama Mohana Reddy Jaggavarapu, Muvvala Venkatanarayana*, Raja Reddy Kamatham, Akula Nagarjuna, Ravi Kumar Cheedarala* and Ravikumar Surepally

Volume 20, Issue 4, 2023

Published on: 15 November, 2022

Page: [484 - 490] Pages: 7

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: Misoprostol, DBU, prostaglandin, intra molecular, isomerization, inhibitor.

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