Examinando por Autor "Vallejos, Javier"

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    Ítem
    Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid
    (MDPI AG, 2014) Simirgiotis, Mario J.; Vallejos, Javier; Areche, Carlos; Sepúlveda, Beatriz
    An enantioselective total synthesis of the natural amino acid (2S,4R,5R)-4,5-dihydroxy-pipecolic acid starting from D-glucoheptono-1, 4-lactone is presented. The best sequence employed as a key step the intramolecular nucleophilic displacement by an amino function of a 6-O-p-toluene-sulphonyl derivative of a methyl D-arabino-hexonate and involved only 12 steps with an overall yield of 19%. The structures of the compounds synthesized were elucidated on the basis of comprehensive spectroscopic (NMR and MS) and computational analysis. © 2014 by the authors; licensee MDPI, Basel, Switzerland.