Enantioselective synthesis of pyrro[3,4-c]quinoline pseudo-natural products

Pseudo natural products (PNPs) are natural product-inspired compounds obtained by unprecedented combination of natural product (NP) fragments in complexity-generating transformations. The pyrrolidine- and tetrahydroquinoline fragments individually occur in numerous NPs with diverse bioactivity, yet not in combination. Herein we report the enantioselectively catalyzed asymmetric synthesis of pyrro [3,4-c]quinoline pseudo-natural products in which these two fragments are combined. The synthesis includes a highly enantioselective 1,3-dipolar cycloaddition between amino acid-derived azomethine ylides and alpha, beta-unsaturated malonic acid esters to yield pyrrolidines followed by a sequence of protection-, reduction- and lactamization steps. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

The study introduces a method for enantioselectively catalyzed asymmetric synthesis of pseudo-natural products, combining pyrrolidine and tetrahydroquinoline fragments to yield a novel compound.