Extending Pummerer Reaction Chemistry. Application to the Total Synthesis of (±)-Dibromoagelaspongin
| Autor: | Ken S. Feldman, Matthew D. Fodor |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Sulfide Metabolite Pummerer rearrangement Dibromoagelaspongin Imidazoles Regioselectivity Total synthesis Stereoisomerism General Chemistry Sulfides Photochemistry Guanidines Biochemistry Combinatorial chemistry Catalysis chemistry.chemical_compound Alkaloids Colloid and Surface Chemistry chemistry Cyclization Sulfoxides Imidazole Pyrroles Oxidation-Reduction |
| Zdroj: | Journal of the American Chemical Society. 130:14964-14965 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | The sponge metabolite dibromoagelaspongin was synthesized in 16 steps from imidazole. The route features two successive oxidative cyclizations with complete control of regiochemistry to deliver the unusual triaminomethane core of the target. These oxidative cyclizations likely resulted from Pummerer-like processes on the imidazole-2-sulfoxide (sulfide) precursors. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|