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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

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A Concise Total Synthesis of (+)-Pedrolide.

Hao Shen¹, Yushang Zhou¹, John L Wood¹

¹Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, Texas 76798, United States.

Journal of the American Chemical Society

|December 22, 2025

Summary

A concise total synthesis of (+)-pedrolide was achieved using an intramolecular Diels-Alder reaction. This method efficiently built the complex carbon skeleton and functionalized the carane moiety through late-stage MHAT reactions.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

(+)-Pedrolide is a complex natural product with a unique tetracyclic structure.
Efficient synthetic routes are crucial for accessing and studying such molecules.

Purpose of the Study:

To develop a concise and efficient total synthesis of (+)-pedrolide.
To explore the utility of key reactions in constructing complex molecular architectures.

Main Methods:

Intramolecular Diels-Alder reaction for tetracyclic skeleton construction.
Late-stage Macrolactonization-Heck Annulation Tandem (MHAT) reactions for carane moiety functionalization.
Stereoselective synthesis starting from (R)-carvone.

Main Results:

Successful and concise total synthesis of (+)-pedrolide.
Demonstrated rapid construction of the tetracyclic core.
Efficiently advanced the highly functionalized carane moiety using MHAT reactions.

Conclusions:

The developed synthetic strategy is effective for accessing (+)-pedrolide.
The study highlights the power of intramolecular Diels-Alder and MHAT reactions in complex molecule synthesis.
This work provides a valuable route for further investigation of pedrolide analogs.