The bromination of the pyrrole was performed following previously reported conditions originating (±)-Agelastatin A (AglA) in 94 % yield, corresponding to an overall yield of 26 % in 6 steps. The one-pot procedures in combination with the late dibenzylamine deprotection hindered the formation of side products and facilitated the chromatographic purifications. In summary, the preparation of mixed DCP was successfully performed with two amines, in a regioselective manner. Benzyl and aryl amines are incorporated preferentially in position 5 in comparison with alkyl amines that are incorporated in position 4 of the cyclopentenone ring. Mixed DCPs undergo thio-Michael addition, followed by reestablishment of the enone by elimination of the alkyl amine (e.g. morpholine), hence increasing the scope of 4-thio-2-enaminones. Additionally, the potential of orthogonally protected DCP was showcased by the preparation of (±)-AglA, a natural product isolated from marine sponge Agelas dendromorpha. Further application of this platform may lead to the development of elegant and efficient strategies for total synthesis of natural products containing diaminocyclopentane cores.