Synthesis of the Marine Natural Product <i>N</i>α-(4-Bromopyrrolyl-2-carbonyl)-<scp>l</scp>-homoarginine, a Putative Biogenetic Precursor of the Pyrrole−Imidazole Alkaloids

Abstract

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.