Biomimetic one-step access to nitraramine from simple C5 units. Revision of the previously reported structure of epinitraramine to nitraramine.
[reaction: see text] A single biomimetic cascade sequence featuring intermolecular followed by intramolecular cyclizations allowed the biomimetic synthesis of nitraramine from simple C5-lysine-derived metabolites. In the course of the study, the structure of epinitraramine was also revisited.
Gravel
Edmond
E
Laboratoire de Pharmacognosie associé au CNRS (UMR 8076, BioCIS), Centre d'Etudes Pharmaceutiques, Université Paris-Sud 11, 5, rue Jean-Baptispte Clément, 92290 Châtenay-Malabry, France.
Poupon
Erwan
E
Hocquemiller
Reynald
R
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D008239:Lysine / Q000031:analogs & derivatives* / Q000737:chemistry*; D018716:Molecular Mimicry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D010880:Piperidines; C508402:nitraramine; D008239:Lysine