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Total Synthesis of Conulothiazole A
Antoine Nitelet1, Phidéline Gérard1, Jimmy Bouche1
1Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques , Université libre de Bruxelles (ULB) , Avenue F. D. Roosevelt 50 , CP160/06, 1050 Brussels , Belgium.
Organic Letters
|May 24, 2019
Summary
Researchers report an efficient total synthesis of conulothiazole A, a chlorinated natural product. Key steps included a novel rhodium-catalyzed hydrogenation and a versatile vinylic Finkelstein reaction for installing the chlorinated alkene.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Conulothiazole A is a complex chlorinated thiazole-containing natural product.
- Efficient synthetic routes are crucial for accessing and studying such molecules.
Purpose of the Study:
- To develop an efficient total synthesis of conulothiazole A.
- To establish key methodologies applicable to the synthesis of chlorinated alkenes.
Main Methods:
- Rhodium-catalyzed enantioselective hydrogenation of a 2-enamido-thiazole intermediate.
- Vinylic Finkelstein reaction for installing the chlorinated alkene moiety.
Main Results:
- Successful and efficient total synthesis of conulothiazole A.
- Demonstration of a novel rhodium-catalyzed hydrogenation for thiazole derivatives.
- Versatile application of the vinylic Finkelstein reaction at multiple synthetic stages.
Conclusions:
- The developed synthetic strategy provides an efficient route to conulothiazole A.
- The key reactions are valuable tools for constructing chlorinated alkenes in natural product synthesis.
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