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Spirodiepoxides in total synthesis: epoxomicin
Sreenivas Katukojvala1, Kristin N Barlett, Stephen D Lotesta
1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA.
Journal of the American Chemical Society
|November 26, 2004
Summary
This study introduces the spirodiepoxide functional group for total synthesis, enabling an efficient route to the proteasome inhibitor epoxomicin. The method yields valuable syn disubstituted ketones and related compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- The spirodiepoxide functional group is a novel motif in organic synthesis.
- Proteasome inhibitors are crucial therapeutic agents, with epoxomicin being a potent example.
Purpose of the Study:
- To report the first application of the spirodiepoxide functional group in total synthesis.
- To develop an efficient synthesis of the proteasome inhibitor epoxomicin using this novel group.
Main Methods:
- Oxidation of allenes to form spirodiepoxides.
- Subsequent chemical transformations of spirodiepoxides to generate diverse functionalized ketones.
Main Results:
- Demonstrated the utility of spirodiepoxides in constructing complex molecular architectures.
- Achieved an efficient total synthesis of epoxomicin.
- Synthesized various syn disubstituted ketones and derivatives, including ortho esters, oxazolines, azido epoxides, and hydroxy ketones with sulfonamide, amide, or azide substituents.
Conclusions:
- The spirodiepoxide functional group is a versatile building block in organic synthesis.
- This methodology provides a strategic approach for accessing complex molecules like epoxomicin.
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