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Open AccessArticle

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.
Molecules 2014, 19(12), 19516-19531; https://doi.org/10.3390/molecules191219516
Received: 7 November 2014 / Revised: 17 November 2014 / Accepted: 18 November 2014 / Published: 26 November 2014
(This article belongs to the Section Organic Chemistry)
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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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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