title: Total synthesis of the akuammiline alkaloid picrinine.
abstract: We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product's carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
authors.forename: Joel M
authors.initials: JM
authors.lastname: Smith
authors.forename: Jesus
authors.initials: J
authors.lastname: Moreno
authors.forename: Ben W
authors.initials: BW
authors.lastname: Boal
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
mesh_terms: D060326:Chemistry Techniques, Synthetic; D026121:Indole Alkaloids / Q000138:chemical synthesis*
chemical_list: D026121:Indole Alkaloids; C528220:picrinine