title: Four-step synthesis of the antimalarial cardamom peroxide via an oxygen stitching strategy.
abstract: A four-step synthesis of the antimalarial terpene cardamom peroxide, a 1,2-dioxepane-containing natural product, is reported from (-)-myrtenal and molecular oxygen. This highly concise route was guided by biosynthetic logic and enabled by an unusual manganese-catalyzed, tandem hydroperoxidation reaction. The absolute configuration of the cardamom peroxide is reported, and its mode of fragmentation following Fe(II)-mediated endoperoxide reduction is established. These studies reveal the generation of reactive intermediates distinct from previously studied endoperoxide natural products.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Xirui
authors.initials: X
authors.lastname: Hu
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Maimone
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D028523:Elettaria / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000962:Antimalarials; D010545:Peroxides; D010100:Oxygen