title: Synthesis of (+/-)-clusianone: high-yielding bridgehead and diketone substitutions by regioselective lithiation of enol ether derivatives of bicyclo[3.3.1]nonane-2,4,9-triones.
abstract: [Structure: see text] A concise synthesis of the polyprenylated acylphloroglucinol natural product, clusianone, in racemic form, is described. An Effenburger cyclization generated a core bicyclo[3.3.1]nonane-trione structure, which was then elaborated by means of regioselective lithiation reactions.
authors.affiliation: School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD UK.
authors.forename: Vincent
authors.initials: V
authors.lastname: Rodeschini
authors.forename: Nadia M
authors.initials: NM
authors.lastname: Ahmad
authors.forename: Nigel S
authors.initials: NS
authors.lastname: Simpkins
mesh_terms: D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000378:metabolism; D028084:Clusiaceae / Q000378:metabolism*; D015394:Molecular Structure
chemical_list: C118110:7-epiclusianone; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds