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...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2014-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/12/19516 |
| _version_ | 1798046025822240768 |
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| author | Mario J. Simirgiotis Javier Vallejos Carlos Areche Beatriz Sepúlveda |
| author_facet | Mario J. Simirgiotis Javier Vallejos Carlos Areche Beatriz Sepúlveda |
| author_sort | Mario J. Simirgiotis |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-04-11T23:30:49Z |
| format | Article |
| id | doaj.art-097ca2f3c2054da69243eae771e766d6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-11T23:30:49Z |
| publishDate | 2014-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-097ca2f3c2054da69243eae771e766d62022-12-22T03:57:07ZengMDPI AGMolecules1420-30492014-11-011912195161953110.3390/molecules191219516molecules191219516Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino AcidMario J. Simirgiotis0Javier Vallejos1Carlos Areche2Beatriz Sepúlveda3Laboratorio de Productos Naturales, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avenida Universidad de Antofagasta 02800, Casilla 170, Antofagasta 1240000, ChileDepartamento de Química, Universidad Católica del Norte, Av. Angamos 610, Antofagasta 1240000, ChileDepartamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago 7800024, ChileDepartamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Quillota 980, Viña del Mar 2520000, ChileAn 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.http://www.mdpi.com/1420-3049/19/12/19516pipecolic acidtotal synthesispiperidineamino acids |
| spellingShingle | Mario J. Simirgiotis Javier Vallejos Carlos Areche Beatriz Sepúlveda Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid Molecules pipecolic acid total synthesis piperidine amino acids |
| 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 | pipecolic acid total synthesis piperidine amino acids |
| url | http://www.mdpi.com/1420-3049/19/12/19516 |
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