Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 30, Pages 10604-+Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500366
Keywords
alkaloids; biomimetic synthesis; lysine; myrioneuron; nitraria
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This Concept article describes how key C-10 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.
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