Pyrrolopiperazinone scaffold is one of the salient features of bromopyrrole alkaloids possessing various biological activities, including cytotoxic, antibiotic, antitumor, and growth inhibitory activities against various cell lines. Due to their potential applications as pharmaceuticals, synthesizing this scaffold has become an attractive research focus. Bromopyrrole alkaloids isolated from Patagonian Bryozoan <i>Aspidostoma giganteum</i> contain phenyl and indole analogues of pyrrolopiperazinone scaffold. Aspidazide A is a unique asymmetric acyl azide containing N-N linkage of two different phenylpyrrolopiperazinones. Aspidostomides D, E, and F contain indolopyrrolopiperazinone in their core structure. The challenging synthesis of these natural products is still unaddressed. This work describes a novel and concise route to synthesize these scaffolds and their derivatives using mild reagents. Both the phenyl as well as indole versions can be accessed using similar routes. α-amino nitriles are used as the starting materials, which can be easily synthesized via well known Strecker synthesis from commercially available aldehydes. The final key cyclization is accessed via Bischler-Napieralski type reaction. The construction of N-N linkage is acheived via electrochemical oxidation.

Synthesis of pyrrolopiperazinone scaffold using novel routes: Application to the total synthesis of bromopyrrole alkaloids isolated from the patagonian bryozoan <i>Aspidostoma giganteum</i>

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Synthesis of pyrrolopiperazinone scaffold using novel routes: Application to the total synthesis of bromopyrrole alkaloids isolated from the patagonian bryozoan Aspidostoma giganteum