title: Total synthesis of the bridged indole alkaloid apparicine.
abstract: An indole-templated ring-closing metathesis or a 2-indolylacyl radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid apparicine. From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institut de Biomedicina, University of Barcelona, Barcelona 08028, Spain. bennasar@ub.edu
authors.forename: M-Lluïsa
authors.initials: ML
authors.lastname: Bennasar
authors.forename: Ester
authors.initials: E
authors.lastname: Zulaica
authors.forename: Daniel
authors.initials: D
authors.lastname: Solé
authors.forename: Tomàs
authors.initials: T
authors.lastname: Roca
authors.forename: Davinia
authors.initials: D
authors.lastname: García-Díaz
authors.forename: Sandra
authors.initials: S
authors.lastname: Alonso
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000470:Alkaloids; C008811:pericalline