To showcase the potential of the new orthogonally protected diaminocyclopentane core, DCP 1c was used as key intermediate for the total synthesis of AglA. The stepwise deprotection would allow bypassing the challenges of amine differentiation, previously encountered by Batey and coworkers. Depicted in Figure is the retrosynthetic analysis of AglA. Due to the incompatibility of dibenzylamine deprotection and the cyclopentene, the initial approach was the formation of B ring upon deprotection of the diallylamine. Afterwards, in the absence of the olefin, deprotection of the dibenzylamine under hydrogenation conditions would pave the way for the formation of D ring. Following the proposed strategy, deallylation of 1c was attempted, however no product was formed despite full conversion (Figure , strategy A). This could be due to the instability of the primary β-amine/enone system. Hence, a second approach was envisioned to protect the carbonyl before deallylation (Figure , strategy B). Unfortunately, the DCP was unreactive in most protection conditions (e.g. acetalization, imine) whereas in the presence of hydrazines and hydroxylamines it underwent decomposition. Despite the poor "redox economy", the only viable approach to inhibit decomposition of the enone was to reduce the carbonyl and oxidize the allylic alcohol just before formation of the B ring (Scheme 3). Hence, DCP 1c was reduced with DIBAL-H to the corresponding allylic alcohol with high diastereoselectivity (> 20:1 dr). Other 1,2-reductive agents were attempted unsuccessfully such as CeCl3/NaBH4 (Luche reduction), L-Selectride and LiAlH4. The crude reaction mixture was reacted with TBSCl and imidazole to yield the corresponding protected alcohol 4 in 92 % yield over the two steps. With the enone masked as a protected allylic alcohol, the deallylation occurred in the presence of N,N-dimethylbarbituric acid (NMDBA) and Pd(PPh3)4. However, the corresponding primary amine was challenging to purify and was therefore trapped with a previously prepared pyrrole acyl chloride. The corresponding amide 5 was obtained in 85 % yield over two steps, without the challenges of amine differentiation engaged by previously reported procedures due to the stepwise amine deprotection. Before deprotecting the dibenzylamine, the formation of ring B was addressed to remove the conflicting olefin. To this end, deprotection of the silyl ether with TBAF afforded the desired alcohol which was used without further purification. The alcohol was readily oxidized to enone 3 with IBX in almost quantitative yield. With 3 in hands, the synthetic plan towards the desired final product was straightforward, since it had been previously studied by Davis and coworkers. Avoiding possible side products (e.g. elimination of the amide leading to the 2,4-enone isomer; dimerization of the α-amino ketone) the reaction was performed in one-pot by first stirring enone 3 with Cs2CO3, followed by addition of Pd/C catalyst and methylamine-carbamoylimidazole. The reaction was stirred under hydrogen atmosphere, leading to deprotection of the dibenzylamine and formation of the urea 9.