TY - JOUR A1 - Innocenti, Riccardo A1 - Lenci, Elena A1 - Menchi, Gloria A1 - Trabocchi, Andrea T1 - Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones JF - Beilstein Journal of Organic Chemistry PY - 2020/// VL - 16 SP - 200 EP - 211 SN - 1860-5397 DO - 10.3762/bjoc.16.23 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.16.23 KW - chemical libraries KW - chemoinformatics KW - Cu-catalysis KW - cycloadditions KW - molecular scaffolds KW - multicomponent reactions N2 - The Cu-catalyzed multicomponent ketone–amine–alkyne (KA2) reaction was combined with a Pauson–Khand cycloaddition to give access of unprecedented constrained spirocyclic pyrrolocyclopentenone derivatives following a DOS couple-pair approach. The polyfunctional molecular scaffolds were tested on the cyclopentenone reactivity to further expand the skeletal diversity, demonstrating the utility of this combined approach in generating novel spiro compounds as starting material for the generation of chemical libraries. The chemoinformatics characterization of the newly-synthesized molecules gave evidence about structural and physicochemical properties with respect to a set of blockbuster drugs, and showed that such scaffolds are drug-like but more spherical and three-dimensional in character than the drugs. ER -