Nitropyrrole natural products: isolation, biosynthesis and total synthesis

Abstract

Nitropyrrole-containing natural products are relatively rare in nature. Known examples are limited to the β-nitropyrrole-containing pyrrolomycins and α-nitropyrrole-containing nitropyrrolins and heronapyrroles. Their unique structures and interesting bioactivity are of ongoing interest to the chemistry community. This review describes the isolation, biological activity, biosynthesis and chemical synthesis of nitropyrrole-containing natural products reported to date.

Marine Pyrrole Alkaloids

“…This rare class of nitropyrroles has attracted some attention from synthetic chemists in recent years. Not least because of previous synthetic work and the promising effects against Gram-positive bacteria, nitropyrroles may represent interesting targets for further drug design [ 115 , 117 , 118 , 120 , 121 , 122 , 123 ].…”

General Synthesis of the Nitropyrrolin Family of Natural Products via Regioselective CO2-Mediated Alkyne Hydration

“…Nitropyrrolins A ( 1 ), B ( 2 ), and D ( 4 ) exhibit cytotoxic activity toward the human colon carcinoma cell line HCT-116 ( 1 IC 50 31.1 μM, 2 IC 50 31.0 μM, and 4 IC 50 5.7 μM) . Inspired by the unique structures, promising biological activity and low abundance in nature, several groups have shown interest in the syntheses of these natural products . Stark et al , and our group have reported successful syntheses of heronapyrroles C and D in 2012 and 2014, respectively.…”

Reactivity of 2-Nitropyrrole Systems: Development of Improved Synthetic Approaches to Nitropyrrole Natural Products

“…The nitropyrrolins A–E 1 – 5 (Figure ) and heronapyrroles A–D 6 – 9 are structurally related pyrroloterpene natural products sharing an unusual 2-nitro-4-alkylpyrrole core . Nitropyrrolins A–E 1 – 5 were isolated from the culture broth of the MAR4 strain CNQ-509, obtained from a marine sediment sample collected off La Jolla, California by Fenical et al in 2010 .…”