Kinetic resolution in a bridgehead lithiation mediated by a chiral bis-lithium amide: assignment of the absolute configuration of clusianone.
A chiral base kinetic resolution of an advanced bicyclic intermediate enabled access to the polyprenylated phloroglucinol natural product (+)-clusianone in enantiomerically pure form. X-ray structure determination of another product obtained by the same method then allowed the absolute stereochemistry of (+)-clusianone to be assigned.
Rodeschini
Vincent
V
School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, U.K.
Simpkins
Nigel S
NS
Wilson
Claire
C
D000577:Amides / Q000737:chemistry*; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D007700:Kinetics; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure
C118110:7-epiclusianone; D000577:Amides; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds; D008094:Lithium