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

Simirgiotis, Mario J.Vallejos, JavierAreche, CarlosSepúlveda, Beatriz2022-12-282022-12-282014Molecules Volume 19, Issue 12, Pages 19516 - 195311 December 20141420-3049https://repositorio.unab.cl/xmlui/handle/ria/29594Indexación: ScopusAn 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.enAmino acidsPipecolic acidPiperidineTotal synthesisConcise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acidArtículoAtribución 4.0 Internacional (CC BY 4.0)10.3390/molecules191219516