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Asymmetric Synthesis of Apratoxin E
Zhuo-Ya Mao1,2, Chang-Mei Si1, Yi-Wen Liu2
1Department of Natural Products Chemistry, School of Pharmacy, Fudan University , 826 Zhangheng Road, Shanghai 201203, China.
This study details an efficient asymmetric synthesis of apratoxin E 2 using a chiral lactone derived from saponins. Olefin cross-metathesis and a novel condensation reagent facilitated key bond formations for this natural product synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Natural Product Synthesis
Background:
- Apratoxin E 2 is a complex natural product with potential biological activities.
- Efficient synthetic routes are crucial for accessing and studying such molecules.
Purpose of the Study:
- To develop an efficient asymmetric synthesis of apratoxin E 2.
- To explore novel strategies for constructing key structural motifs.
Main Methods:
- Utilized a chiral lactone (8) recycled from saponin glycosides.
- Employed olefin cross-metathesis (CM) for double bond formation.
- Applied pentafluorophenyl diphenylphosphinate as a condensation reagent for macrocyclization.
Main Results:
- Successfully synthesized the non-peptide fragment (6) using a "from nature to nature" approach.
- Demonstrated the efficacy of CM as an alternative synthetic strategy.
- Identified an efficient reagent for macrocyclization.
Conclusions:
- Developed a viable and efficient asymmetric synthesis of apratoxin E 2.
- Highlighted the utility of natural product-derived chiral synthons.
- Showcased innovative synthetic methodologies for complex molecule construction.
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