Rippel, RafaelPinheiro, LuísLopes, MónicaLourenço, AnaFerreira, Luísa M.Branco, Paula S.2020-10-092020-10-092020-02-12PURE: 20261279PURE UUID: 13b27811-2046-41fb-9365-7f351d461137Scopus: 85079513993PubMed: 32059504PubMedCentral: PMC7070370WOS: 000522454500033ORCID: /0000-0001-8474-3925/work/81722211ORCID: /0000-0001-7358-3428/work/81722231ORCID: /0000-0002-7312-8596/work/81722560http://hdl.handle.net/10362/105370Associate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UIDB/50006/2020). Grant number SFRH/BD/136692/2018 from FCT/MCTES.The synthesis of an unreported 2-aminopyrrolidine-1-carboxamidine unit is here described for the first time. This unusual and promising structure was attained through the oxidative decarboxylation of amino acids using the pair of reagents, silver(I)/peroxydisulfate (Ag(I)/S2O82−) followed by intermolecular (in the case of L-proline derivative) and intramolecular trapping (in the case of acyl L-arginine) by N-nucleophiles. The L-proline approach has a broader scope for the synthesis of 2-aminopyrrolidine-1-carboxamidine derivatives, whereas the intramolecular cyclization afforded by the L-acylarginines, when applied, results in higher yields. The former allowed the first synthesis of cernumidine, a natural alkaloid isolated in 2011 from Solanum cernuum Vell, as its racemic form.3680001engAmino acid decarboxylationCernumidineCyclic-guanidineRadical decarboxylationAnalytical ChemistryChemistry (miscellaneous)Molecular MedicinePharmaceutical ScienceDrug DiscoveryPhysical and Theoretical ChemistryOrganic Chemistryjournal article10.3390/molecules25040797https://www.scopus.com/pages/publications/85079513993