Synthesis of Rhodocorane L Using Gold-Catalyzed Dearomative Spirocyclization

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Medicinal Chemistry

Background:

• Rhodocorane L, an acorane-type terpenoid, was isolated from the fungus *Rhodotus palmatus*.
• This compound possesses a unique tricyclic scaffold with a spiro[4.5] bicycle.
• The compound exhibits notable antifungal activity.

Purpose of the Study:

• To achieve the first total synthesis of rhodocorane L.
• To explore and implement novel synthetic methodologies.
• To confirm the structure and biological activity of rhodocorane L.

Main Methods:

• The synthesis employed a 17-step longest linear sequence.
• Key steps included diastereoselective cuprate addition.
• A gold-catalyzed dearomative spirocyclization was a crucial transformation.
• An intramolecular aldol reaction was also utilized.

Main Results:

• The first total synthesis of rhodocorane L was successfully accomplished.
• A novel catalyst-controlled asymmetric dearomative spirocyclization was developed and applied.
• The synthesis validated the structural assignment and potential of rhodocorane L.

Conclusions:

• The total synthesis of rhodocorane L provides a scalable route to this antifungal agent.
• The developed dearomative spirocyclization represents a significant advancement in synthetic organic chemistry.
• This work opens avenues for the development of new antifungal compounds based on the acorane scaffold.