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Updated: Feb 3, 2026
06:45
Use of Electron Paramagnetic Resonance in Biological Samples at Ambient Temperature and 77 K
Published on: January 11, 2019
9.8K
Asymmetric Total Synthesis of the Gastroprotective Microbial Agent AI-77-B
Arun K Ghosh1, Alexander Bischoff1, John Cappiello1
1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.
European Journal of Organic Chemistry
|November 6, 2018
Summary
This study details the first enantioselective total synthesis of AI-77-B, a potent antiulcerogenic microbial agent. The convergent synthesis efficiently combines key fragments to produce optically active AI-77-B.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- AI-77-B is a microbial agent with significant antiulcerogenic properties.
- The development of efficient synthetic routes for complex natural products is crucial for drug discovery.
Purpose of the Study:
- To achieve the first enantioselective total synthesis of the pseudopeptide microbial agent AI-77-B.
- To establish a convergent synthetic strategy for constructing AI-77-B.
Main Methods:
- Convergent synthesis involving a Diels-Alder reaction to form a dihydroisocoumarin fragment.
- Stereoselective synthesis of an alkynyl ester via allylation or an anti-aldol reaction.
- Generation of stereocenters in the hydroxy amino acid moiety using syn-aldol reactions, Curtius rearrangement, and aldehyde homologation.
Main Results:
- Successful enantioselective total synthesis of AI-77-B.
- Efficient assembly of the dihydroisocoumarin and hydroxy amino acid fragments.
- Production of optically active AI-77-B.
Conclusions:
- The developed synthetic route is effective for producing AI-77-B.
- This synthesis provides a foundation for further investigation and potential production of AI-77-B.
- The study highlights the utility of specific reactions for constructing complex chiral molecules.
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