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Scalable Total Synthesis of (-)-Vinigrol
Xuerong Yu1, Lianghong Xiao1, Zechun Wang1
1Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
Journal of the American Chemical Society
|February 16, 2019
Summary
Researchers developed an efficient synthesis for the complex natural product vinigrol, yielding over 600 mg. This method highlights macrocyclic stereocontrol and a transannular Diels-Alder reaction for potent TNF-α modulation.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Vinigrol is a complex natural product with significant pharmacological potential.
- Its structure presents a considerable synthetic challenge.
- Vinigrol is known to modulate Tumor Necrosis Factor-alpha (TNF-α).
Purpose of the Study:
- To develop a novel and efficient synthetic route for (-)-vinigrol.
- To achieve a high-yielding asymmetric synthesis of this complex molecule.
- To demonstrate the utility of specific synthetic strategies in natural product synthesis.
Main Methods:
- Employed macrocyclic stereocontrol strategies.
- Utilized a transannular Diels-Alder reaction.
- Developed a multi-step asymmetric synthesis pathway.
Main Results:
- Successfully completed the asymmetric synthesis of (-)-vinigrol.
- Produced over 600 mg of the target natural product.
- Demonstrated the efficiency and scalability of the new synthetic route.
Conclusions:
- The developed synthetic route is efficient for producing complex natural products like vinigrol.
- Macrocyclic stereocontrol and transannular Diels-Alder reactions are powerful tools in organic synthesis.
- This synthesis provides ample material for further pharmacological investigation of vinigrol and its TNF-α modulating capabilities.
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