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.
[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.
Rodeschini
Vincent
V
School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD UK.
Ahmad
Nadia M
NM
Simpkins
Nigel S
NS
D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000378:metabolism; D028084:Clusiaceae / Q000378:metabolism*; D015394:Molecular Structure
C118110:7-epiclusianone; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds