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Synthetic Approaches to A Challenging and Unusual Structure—An Amino-Pyrrolidine Guanine Core

LAQV-REQUIMTE, NOVA School of Science and Technology, 2829-516 Caparica, Portugal
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Molecules 2020, 25(4), 797; https://doi.org/10.3390/molecules25040797 (registering DOI)
Received: 10 January 2020 / Revised: 7 February 2020 / Accepted: 10 February 2020 / Published: 12 February 2020
(This article belongs to the Special Issue Application of Organic Synthesis to Bioactive Compounds)
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.
Keywords: amino acid decarboxylation; cyclic-guanidine; Cernumidine; radical decarboxylation amino acid decarboxylation; cyclic-guanidine; Cernumidine; radical decarboxylation
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MDPI and ACS Style

Rippel, R.; Pinheiro, L.; Lopes, M.; Lourenço, A.; Ferreira, L.M.; Branco, P.S. Synthetic Approaches to A Challenging and Unusual Structure—An Amino-Pyrrolidine Guanine Core. Molecules 2020, 25, 797.

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