A divergent approach for asymmetric syntheses of (+)-spicigerine, (+)-cassine and their 3-epimers

An efficient approach for asymmetric synthesis of (+)-spicigerine, (+)-cassine and their 3-epimers has been developed through the intramolecular diastereoselective tandem addition/cyclisation process of α-chiral aldimine 9 with methylmagnesium bromide and the asymmetric addition of nucleophilic reagents to aminal 14. Moreover, the first asymmetric synthesis of (+)-spicigerine has been achieved in this manuscript. In this synthetic strategy, the asymmetric syntheses of (+)-spicigerine and (+)-cassine was achieved in a 14% overall yield and nine steps and an 18% overall yield and seven steps from cheap α-chiral aldimine 9, respectively.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide