Total syntheses of (±)-21-oxogelsemine (3) and (±)-gelsemine (1) are described. Free radical cyclizations play important roles in constructing the tricyclic core (40 → 41) and oxindole (93 → 96) substructures of the target alkaloids, and an isomerization−cyclization strategy (101 → 102) was used to complete construction of the gelsemine cage. Observations made along the way include intramolecular 1,4- and 1,6-hydrogen atom transfers (64 → 65 and 40 → 47) and a free radical cyclization-fragmentation sequence (85 → 86 + 87). A retroaldol−aldol strategy for adjusting oxindole stereochemistry in gelsemine-like structures is also described (72 → 74 and 86 → 87).

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