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Total synthesis of (+)-asteltoxin
Khee Dong Eom1, J Venkat Raman, Heejin Kim
1Department of Chemistry, University of Alabama, Tuscaloosa, Alabama 35487, USA.
Journal of the American Chemical Society
|May 2, 2003
Summary
Researchers synthesized (+)-asteltoxin using a novel Horner-Emmons olefination. A key Lewis acid-catalyzed rearrangement efficiently created a complex quaternary center, mimicking the natural product
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Stereoselective Synthesis
Background:
- (+)-Asteltoxin is a complex natural product with a unique structure.
- Previous synthetic routes have faced challenges in constructing its densely functionalized core.
Purpose of the Study:
- To develop a convergent and stereoselective synthesis of (+)-asteltoxin.
- To establish a novel rearrangement methodology for constructing sterically hindered quaternary centers.
Main Methods:
- Convergent synthesis strategy employing Horner-Emmons olefination.
- Stereoselective construction of a quaternary center via Lewis acid-catalyzed pinacol-type rearrangement of an epoxy silyl ether.
Main Results:
- Successful synthesis of (+)-asteltoxin.
- Efficient and stereoselective formation of a congested quaternary carbon center.
- Demonstration of a rearrangement methodology applicable to complex natural product synthesis.
Conclusions:
- The developed synthetic route provides an efficient pathway to (+)-asteltoxin.
- The pinacol-type rearrangement is a powerful tool for stereocontrolled synthesis of complex molecules.
- This methodology holds promise for the synthesis of other structurally intricate natural products.
