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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
A Total Synthesis of (±)-Leuconodines D and E
Jing Zhang1,2, Fu-She Han1
1CAS Key Lab of High-Performance Synthetic Rubber and Its Composite Materials , Changchun Institute of Applied Chemistry, Chinese Academy of Sciences , 5625 Renmin Street , Changchun , Jilin 130022 , China.
Researchers developed a novel synthetic route for leuconodines D and E. This efficient synthesis rapidly constructs the complex diaza[5.5.6.6]fenestrane core, enabling first-time total synthesis of leuconodine E.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Leuconodines D and E are complex natural products with potential biological activity.
- Previous synthetic routes to similar structures are often lengthy and inefficient.
Purpose of the Study:
- To develop a novel and efficient synthetic strategy for (±)-leuconodines D and E.
- To establish a concise total synthesis of these complex molecules.
Main Methods:
- Utilized a palladium-catalyzed aerobic oxidative Heck cross-coupling reaction.
- Employed epoxidative cyclization for pyrroloindole assembly.
- Incorporated ring-closing metathesis for piperidine ring construction.
Main Results:
- Successfully synthesized (±)-leuconodine E in a 10-step linear sequence.
- Achieved a concise 12-step total synthesis of (±)-leuconodine D.
- Efficiently constructed the challenging diaza[5.5.6.6]fenestrane core.
Conclusions:
- The developed synthetic route offers a rapid and efficient method for accessing leuconodines D and E.
- This strategy provides a valuable platform for the synthesis of related complex natural products.
- The synthesis highlights the utility of modern catalytic methods in complex molecule construction.
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