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Synthesis of Polycyclic Ethers by Two-Directional Double Ring-Closing Metathesis
1School of Chemistry University of Nottingham University Park, Nottingham NG7 2RD (UK).
Angewandte Chemie (International Ed. in English)
|January 29, 2000
Summary
Researchers developed a new synthesis strategy for complex cyclic ethers using two-directional double ring-closing metathesis. This method efficiently constructs fused tricyclic ethers, offering a novel route to brevetoxins and ciguatoxins.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Natural Product Synthesis
Background:
- Tricyclic ethers are core structures in potent marine toxins like brevetoxins and ciguatoxins.
- Existing synthetic methods face challenges in efficiently constructing the complex fused ring systems of these natural products.
Purpose of the Study:
- To develop a novel and efficient strategy for synthesizing trans-fused tricyclic ethers.
- To establish a new synthetic route applicable to brevetoxins and ciguatoxins.
Main Methods:
- Utilized two-directional double ring-closing metathesis reactions.
- Employed precursors bearing various unsaturated functionalities including alkenes, allylic ethers, enol ethers, and alkynyl ethers.
Main Results:
- Successfully constructed trans-fused tricyclic ethers incorporating six-, seven-, eight-, and nine-membered rings.
- Demonstrated the versatility of the double cyclization strategy with different precursor types.
Conclusions:
- The developed two-directional double ring-closing metathesis provides a powerful new strategy for constructing complex fused polycyclic ether scaffolds.
- This approach offers a promising pathway for the total synthesis of brevetoxins and ciguatoxins.