Synthesis of the marine natural product nalpha-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine, a putative biogenetic precursor of the pyrrole-imidazole alkaloids.

Lysine is proposed as an alternative biosynthetic precursor of the pyrrole-imidazole alkaloids frequently found in marine sponges. As a putative key intermediate, the natural product Nalpha-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine (1) from the sponge Agelas wiedenmayeri was synthesized in the solid phase starting from Fmoc/Pmc-protected L-homoarginine and in solution starting from readily available L-lysine methyl ester.