title: An Efficient Synthesis of (±)-Dehaloperophoramidine.
abstract: Perophoramidine and communesin F are structurally related indole alkaloids with an intriguing polycyclic core containing vicinal all-carbon quaternary stereocenters. Dehaloperophoramidine is a dehalogenated synthetic analogue of perophoramidine. Synthetic studies toward the total synthesis of dehaloperophoramidine have led to the discovery of two novel domino processes, the first encompassing four steps and resulting in the formation of an ortho-amide. A thorough study of the reactivity of the ortho-amide functionality revealed the second domino reaction and ultimately yielded the target molecule. The vicinal all-carbon quaternary stereocenters having trans relative stereochemistry are constructed early in the reaction sequence by employing Overman's samarium mediated reductive dialkylation procedure. Described are the synthetic studies that led to the final eight-step synthesis of dehaloperophoramidine.
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , 22100 Lund, Sweden.
authors.forename: Anita
authors.initials: A
authors.lastname: Hoang
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , 22100 Lund, Sweden.
authors.forename: Kirill
authors.initials: K
authors.lastname: Popov
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , 22100 Lund, Sweden.
authors.forename: Peter
authors.identifier: 0000-0001-9416-1283
authors.initials: P
authors.lastname: Somfai
mesh_terms: D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D006846:Hydrocarbons, Halogenated; C472225:perophoramidine