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

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 deriv...

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Autores principales: Simirgiotis, Mario J., Vallejos, Javier, Areche, Carlos, Sepúlveda, Beatriz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271146/
https://www.ncbi.nlm.nih.gov/pubmed/25432006
http://dx.doi.org/10.3390/molecules191219516
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author Simirgiotis, Mario J.
Vallejos, Javier
Areche, Carlos
Sepúlveda, Beatriz
author_facet Simirgiotis, Mario J.
Vallejos, Javier
Areche, Carlos
Sepúlveda, Beatriz
author_sort Simirgiotis, Mario J.
collection PubMed
description 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.
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spelling pubmed-62711462018-12-28 Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid Simirgiotis, Mario J. Vallejos, Javier Areche, Carlos Sepúlveda, Beatriz Molecules Article 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. MDPI 2014-11-26 /pmc/articles/PMC6271146/ /pubmed/25432006 http://dx.doi.org/10.3390/molecules191219516 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Simirgiotis, Mario J.
Vallejos, Javier
Areche, Carlos
Sepúlveda, Beatriz
Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid
title Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid
title_full Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid
title_fullStr Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid
title_full_unstemmed Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid
title_short Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid
title_sort concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271146/
https://www.ncbi.nlm.nih.gov/pubmed/25432006
http://dx.doi.org/10.3390/molecules191219516
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