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A concise total synthesis of breitfussin A and B
Sunil Kumar Pandey1, Yngve Guttormsen, Bengt Erik Haug
1University of Bergen , Department of Chemistry and Centre for Pharmacy, Allégt 41, NO-5007 Bergen, Norway.
Abstract:
The first total synthesis of breitfussin A and B is described. The approach features two palladium-catalyzed cross-couplings installing the indole and pyrrole onto the oxazole core and selective lithiation/iodination of a common indole-oxazole fragment providing 2,4-diiodinated or 2-iodinated oxazoles as potential precursors for breitfussin A and B, respectively. An unexpected acid promoted deiodination was utilized in the synthesis of breitfussin B. Comparison of the synthetic material with previously reported spectral data of isolated breitfussin A and B verified the structure of the breitfussin framework.
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