title: A concise total synthesis of breitfussin A and B.
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.
authors.affiliation: University of Bergen , Department of Chemistry and Centre for Pharmacy, Allégt 41, NO-5007 Bergen, Norway.
authors.forename: Sunil Kumar
authors.initials: SK
authors.lastname: Pandey
authors.forename: Yngve
authors.initials: Y
authors.lastname: Guttormsen
authors.forename: Bengt Erik
authors.initials: BE
authors.lastname: Haug
authors.forename: Christian
authors.initials: C
authors.lastname: Hedberg
authors.forename: Annette
authors.initials: A
authors.lastname: Bayer
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D037402:Hydrozoa / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010080:Oxazoles / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D001688:Biological Products; D006842:Hydrocarbons, Brominated; D007211:Indoles; D010080:Oxazoles; D011758:Pyrroles; C000595759:breitfussin A; C000595760:breitfussin B