Abstract This report describes a new synthetic approach to symmetrical diamino-substituted Tröger's base analogues, allowing the synthesis of 1, 7-, and 4, 10-diamino derivatives with no additional substituents and of 3, 9-diamino derivative with methyl groups in the 1-, 4-, 7- and 10-positions. The synthesis uses regioselective nitration of dihalo-substituted-or tetrahalo-substituted Tröger's bases followed either by hydrogenation of the nitro functions ...