Total Synthesis and Structural Revision of (-)-Garvensintriol.
Yifei Zhang1,2,3, Chuanfang Zhao1,2, Bitao Wei1,2
1State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
Journal of Natural Products
|June 3, 2026
Summary
Researchers synthesized and revised the structure of (-)-garvensintriol, a cytotoxic styryllactone. The study corrected its stereochemistry and lactone ring size, confirming its identity with (-)-3-deoxycardiobutanolide.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Styryllactones are a class of natural products with potential cytotoxic activity.
- (-)-Garvensintriol, isolated from *Goniothalamus arvensis*, was previously assigned a specific structure.
- The precise stereochemistry and structural class of natural products are crucial for understanding their biological activity.
Purpose of the Study:
- To achieve the stereoselective total synthesis of (-)-garvensintriol.
- To revise and unambiguously confirm the structure of (-)-garvensintriol.
- To investigate the relationship between (-)-garvensintriol and other related natural products.
Main Methods:
- Stereoselective total synthesis.
- Single-crystal X-ray diffraction analysis.
- Density Functional Theory (DFT) calculations.
- Spectroscopic data analysis.
Main Results:
- The stereoselective total synthesis of (-)-garvensintriol was successfully accomplished.
- The structure was revised to a five-membered γ-butyrolactone, correcting the initial assignment of a δ-lactone.
- The revised structure was confirmed through synthesis and spectroscopic data, showing identity with (-)-3-deoxycardiobutanolide.
Conclusions:
- The correct structure of (-)-garvensintriol has been established through synthesis and structural analysis.
- (-)-Garvensintriol and (-)-3-deoxycardiobutanolide are proposed to be the same natural product.
- This work provides a foundation for further investigation into the biological activities of this styryllactone class.
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