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.