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


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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 N-alpha-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine (1) from the sponge Agelas wiedenmayeri was synthesized in the solid phase starting from the Fmoc/Pmc-protected L-homoarginine and in solution starting from readily available L-lysine methyl ester.



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4295
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Lindel, T. , Hochgürtel, M. , Assmann, M. and Köck, M. (2000): Synthesis of the marine natural product N-alpha-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine, a putative biogenetic precursor of the pyrrole-imidazole alkaloids , Journal of Natural Products, 63 , pp. 1566-1569 .


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