Transbromination of brominated pyrrole and imidazole derivatives: Synthesis of the C11N5 marine alkaloid stevensine

Article abstract of DOI:10.1016/0040-4039(96)01888-6

The marine sponge alkaloid stevensine (3) has been synthesized from the related C₁₁N₅ alkaloid, hymenin (1). The key transformation involves a regioselective protodebromination/transbromination event of 4'-bromohymenin (2) to install the olefin in 3. Such processes are seldom used for synthetic purposes but appear to be highly applicable to the C₁₁N₅ family of marine alkaloids.