Synthesis of (+)-coronafacic acid

Area of Science:

• Organic Chemistry
• Natural Product Synthesis

Background:

• Coronafacic acid is a key component of coronatine, a phytotoxin produced by *Pseudomonas syringae*.
• The development of efficient synthetic routes to coronafacic acid is important for understanding its biological activity and for potential applications.

Purpose of the Study:

• To achieve an enantioselective synthesis of (+)-coronafacic acid.
• To explore novel catalytic methods for constructing the core cyclopentanone and bicyclic enone structures.

Main Methods:

• Rhodium-catalyzed cyclization of an alpha-diazoester to form a cyclopentanone intermediate with high enantiomeric purity.
• Iron-mediated cyclocarbonylation of an alkenyl cyclopropane to construct a bicyclic enone system.
• Subsequent hydrogenation and functional group manipulation to yield the target natural product.

Main Results:

• Successful enantioselective synthesis of (+)-coronafacic acid.
• High enantiomeric purity of the key cyclopentanone intermediate was achieved via rhodium catalysis.
• The Fe-mediated cyclocarbonylation provided efficient access to the bicyclic enone core structure.

Conclusions:

• The developed synthetic strategy provides an effective route to (+)-coronafacic acid.
• The study highlights the utility of rhodium and iron catalysis in complex molecule synthesis.
• This work contributes to the synthetic methodology for accessing phytotoxins and related natural products.