Enantioselective Total Synthesis of (+)-Subincanadine F via Organo-SOMO Catalysis.

The asymmetric total synthesis of (+)-subincanadine F has been achieved in only 9 steps from commercial tryptamine. A key step involves an Organo-SOMO-catalyzed α-arylation of aldehydes to construct the azepino[4,5-b]indole core. Finally, a subsequent intramolecular aza-Michael addition process leads to the formation of the 1-azabicyclo[4.3.1]decane framework. In addition, this Organo-SOMO catalytic strategy features a broad substrate scope, with diverse functionalized products afforded in generally moderate to good yields and good to excellent enantioselectivities.