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Molecules 2014, 19(12), 19516-19531; doi:10.3390/molecules191219516

Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid

1
Laboratorio de Productos Naturales, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avenida Universidad de Antofagasta 02800, Casilla 170, Antofagasta 1240000, Chile
2
Departamento de Química, Universidad Católica del Norte, Av. Angamos 610, Antofagasta 1240000, Chile
3
Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago 7800024, Chile
4
Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Quillota 980, Viña del Mar 2520000, Chile
*
Author to whom correspondence should be addressed.
Received: 7 November 2014 / Revised: 17 November 2014 / Accepted: 18 November 2014 / Published: 26 November 2014
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [633 KB, uploaded 26 November 2014]   |  

Abstract

An enantioselective total synthesis of the natural amino acid (2S,4R,5R)-4,5-di-hydroxy-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. View Full-Text
Keywords: pipecolic acid; total synthesis; piperidine; amino acids pipecolic acid; total synthesis; piperidine; amino acids
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Simirgiotis, M.J.; Vallejos, J.; Areche, C.; Sepúlveda, B. Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid. Molecules 2014, 19, 19516-19531.

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