Biomimetic Total Synthesis of Lamellarin L by Coupling of Two Different Arylpyruvic Acid Units

Abstract

Reaction of the ethyl 3-arylpyruvate 5 a with the methyl 2-bromo-3-arylpyruvate 6 b in the presence of the 2-arylethylamine 4 afforded the pyrrole derivative 10, which could be transformed into lamellarin L (1) in five steps. The synthesis proceeds with 38 % overall yield and mimics the probable biosynthesis of these marine alkaloids.