The concise and efficient total synthesis of (±)-tetraponerine-2 (T2) and (±)-tetraponerine-4 (T4) was achieved in 9% and 14% overall yield, respectively. The key step included the diastereoselective gold(I)catalyzed intramolecular dehydrative amination of an allylic alcohol-tethered sulfamide to produce the cis-1,3-diamine moiety. The resulting olefinic side chain was then elaborated by cross-metathesis and cyclized to a fivemembered pyrrolidine or a six-membered piperidine ring by intramolecular Mitsunobu N-alkylation. The unique tricyclic core of the (±)-tetraponerines was completed through cyclic sulfamide cleavage followed by aminal formation using 4-bromobutanal. This flexible synthetic strategy allows for the variation of the ring size, C-5 alkyl side chain length, and stereochemistry, which enables the preparation of diverse tetraponerine analogs for biological study.