Based on a suggested biogenetic sequence, a sarpagine-type indole alkaloid, gardnerine (7), was converted into three novel Gelsemium alkaloids, gelselegine (4), gelsenicine (6), and gelsedine (5). This first synthesis of these alkaloids involves stereoselective skeletal rearrangements, such as indole to oxindole transformations and conversion of humantenine-type compounds to gelselegine,as well as the synthesis of a characteristic N-a-methoxyoxindole function.