Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid

dc.creatorSimirgiotis, Mario J.
dc.creatorVallejos, Javier
dc.creatorAreche, Carlos
dc.creatorSepúlveda, Beatriz
dc.date.accessioned2022-12-28T16:45:43Z
dc.date.accessioned2024-05-02T14:57:57Z
dc.date.available2022-12-28T16:45:43Z
dc.date.available2024-05-02T14:57:57Z
dc.date.created2022-12-28T16:45:43Z
dc.date.issued2014
dc.identifierMolecules Volume 19, Issue 12, Pages 19516 - 195311 December 2014
dc.identifier1420-3049
dc.identifierhttps://repositorio.unab.cl/xmlui/handle/ria/29594
dc.identifier10.3390/molecules191219516
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/9260811
dc.description.abstractAn 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.
dc.languageen
dc.publisherMDPI AG
dc.rightshttps://creativecommons.org/licenses/by/4.0/deed.es
dc.rightsAtribución 4.0 Internacional (CC BY 4.0)
dc.subjectAmino acids
dc.subjectPipecolic acid
dc.subjectPiperidine
dc.subjectTotal synthesis
dc.titleConcise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid
dc.typeArtículo


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