Subincanadines A−C, Novel Quaternary Indole Alkaloids from Aspidosperma s ubincanum

Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.01,5]undecane moiety, subincanadines A−C (1 − 3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]decane moiety, subincanadine F (6), have been isolated from the barks of Aspidosperma subincanum Mart, and the structures of 1 − 6 and the stereochemistry of 1 − 3 were elucidated by spectroscopic data and chemical means.