Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid
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Fecha
2014
Profesor/a Guía
Facultad/escuela
Idioma
en
Título de la revista
ISSN de la revista
Título del volumen
Editor
MDPI AG
Nombre de Curso
Licencia CC
Atribución 4.0 Internacional (CC BY 4.0)
Licencia CC
https://creativecommons.org/licenses/by/4.0/deed.es
Resumen
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.
Notas
Indexación: Scopus
Palabras clave
Amino acids, Pipecolic acid, Piperidine, Total synthesis
Citación
Molecules Volume 19, Issue 12, Pages 19516 - 195311 December 2014
DOI
10.3390/molecules191219516