The reactivity of 16-nitroindolenine (4), a byproduct of the aromatic
nitration of vincadifformine (1), has been studied. In TFA 4 yielded 1
0-nitrovincadifformine (3) whereas acid hydrolytic treatment led to th
e tetracyclic oxindole structure (8) by cleavage of the 2-16 bond. Red
uction of 4 (SnCl2 or hydrogenolysis) allowed recovery of 1 in good yi
eld.