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Synthesis of Rhodocorane L Using Gold-Catalyzed Dearomative Spirocyclization.

Emily A Shimizu¹, Scott D Rychnovsky¹

¹Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, Irvine, California 92697, United States.

Organic Letters

|June 2, 2025

Summary

This summary is machine-generated.

Researchers report the first total synthesis of rhodocorane L, an acorane-type terpenoid with antifungal properties. This achievement highlights a novel catalyst-controlled asymmetric dearomative spirocyclization strategy.

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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.