Circular dichroism of tail-to-tail bisbenzyliso-quinoline and the absolute configuration of daurisoline isolated from Menispermum dauricum

Since two asymmetric centres are usually present in the bisbenzylisoquinolines, the circular dichroism is known to be an important method to elucidate their stereochemistry. We studied the relationships of the CD spectra with the stereochemistry of synthetic RR-(1), SS-(2), RS-daurisoline (3) and SR-daurisoline (4). By comparision of the CD spectrum of natural daurisoline (1) from Menispermum dauricum (Menispermaceae) with those of synthetic enantiomers, the absolute configuration was established as RR-daurisoline (1).