title: Manipulating Simple Reactive Chemical Units: Fishing for Alkaloids from Complex Mixtures.
abstract: This Concept article describes how key C10 molecular scaffolds, too reactive to be obtained through classical multistep synthesis, were targeted in the most simple reaction conditions, reproducing those that may be encountered in living cells. The rationale was that small amounts of these reactive intermediates might be formed in situ from cheap and abundant reactants (i.e., glutaraldehyde and tetrahydropyridine) resulting, upon further rearrangement in "complex mixtures" from which natural substances would arise. From five types of mixtures, at least six full carbon skeletons of known natural substances were formed spontaneously. This work also led to the discovery of new plausible biosynthetic achiral precursors in the Nitraria metabolism.
authors: Laboratoire de Pharmacognosie associé au CNRS, UMR 8076 BioCIS, LabEx LERMIT, Université Paris-Sud, Faculté de Pharmacie, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry (France). erwan.poupon@u-psud.fr.
authors: Erwan
authors: E
authors: Poupon
authors: CEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, LabEx LERMIT, 91191 Gif-sur-Yvette (France).
authors: Edmond
authors: E
authors: Gravel
keywords: alkaloids; biomimetic synthesis; lysine; myrioneuron; nitraria