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A Concise Total Synthesis of Breitfussin A and B
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2015 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, no 1, 122-125 p.Article in journal (Refereed) Published
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Abstract [en]

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.

Place, publisher, year, edition, pages
2015. Vol. 17, no 1, 122-125 p.
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Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-120323DOI: 10.1021/ol503348nISI: 000347506200032PubMedID: 25514017OAI: oai:DiVA.org:umu-120323DiVA: diva2:928652
Available from: 2016-05-16 Created: 2016-05-16 Last updated: 2016-05-16Bibliographically approved

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Haug, Bengt ErikHedberg, ChristianBayer, Annette
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