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Divergent syntheses of complex Veratrum alkaloids
Yinliang Guo1, Runting Fang2, Yang Jiao1
1Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering, Peking University, Beijing, China.
This study presents a unified synthetic strategy for complex Veratrum alkaloids. It achieves the total synthesis of highly oxidized cevanine subtypes, including (-)-zygadenine and (-)-germine.
Area of Science:
- Natural product synthesis
- Organic chemistry
- Medicinal chemistry
Background:
- Veratrum alkaloids possess complex structures and diverse bioactivities, including antihypertensive and antimicrobial effects.
- While synthesis of some subtypes is advanced, highly oxidized cevanine subtypes remain challenging targets.
Purpose of the Study:
- To develop a unified synthetic approach for highly oxidized Veratrum alkaloids.
- To achieve the total synthesis of specific cevanine subtypes.
Main Methods:
- Utilized a previously established strategy for hexacyclic carbon skeleton construction.
- Employed a stereoselective intramolecular Diels-Alder reaction and radical cyclization.
- Incorporated a sequence of redox manipulations and late-stage neighboring-group participation.
Main Results:
- Successfully synthesized (-)-zygadenine, (-)-germine, (-)-protoverine, and the alkamine of veramadine A.
- Demonstrated a unified approach applicable to highly oxidized Veratrum alkaloids.
Conclusions:
- The developed strategy provides efficient access to complex Veratrum alkaloids.
- This work expands the synthetic accessibility of challenging natural products with potential therapeutic applications.
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