Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid

Mario J. Simirgiotis, Javier Vallejos, Carlos Areche, Beatriz Sepúlveda

Resultado de la investigación: Article

2 Citas (Scopus)

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.

Idioma originalEnglish
Páginas (desde-hasta)19516-19531
Número de páginas16
PublicaciónMolecules
Volumen19
N.º12
DOI
EstadoPublished - 1 dic 2014

Huella dactilar

Hydroxy Acids
Toluene
Lactones
amino acids
Nuclear magnetic resonance
Derivatives
Amino Acids
synthesis
toluene
nuclear magnetic resonance
acids
4,5-di-hydroxy-pipecolic acid

ASJC Scopus subject areas

  • Organic Chemistry
  • Pharmaceutical Science
  • Physical and Theoretical Chemistry
  • Chemistry (miscellaneous)
  • Analytical Chemistry
  • Molecular Medicine
  • Drug Discovery

Citar esto

Simirgiotis, M. J., Vallejos, J., Areche, C., & Sepúlveda, B. (2014). Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid. Molecules, 19(12), 19516-19531. https://doi.org/10.3390/molecules191219516
Simirgiotis, Mario J. ; Vallejos, Javier ; Areche, Carlos ; Sepúlveda, Beatriz. / Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid. En: Molecules. 2014 ; Vol. 19, N.º 12. pp. 19516-19531.
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Simirgiotis, MJ, Vallejos, J, Areche, C & Sepúlveda, B 2014, 'Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid', Molecules, vol. 19, n.º 12, pp. 19516-19531. https://doi.org/10.3390/molecules191219516

Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid. / Simirgiotis, Mario J.; Vallejos, Javier; Areche, Carlos; Sepúlveda, Beatriz.

En: Molecules, Vol. 19, N.º 12, 01.12.2014, p. 19516-19531.

Resultado de la investigación: Article

TY - JOUR

T1 - Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid

AU - Simirgiotis, Mario J.

AU - Vallejos, Javier

AU - Areche, Carlos

AU - Sepúlveda, Beatriz

PY - 2014/12/1

Y1 - 2014/12/1

N2 - 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.

AB - 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.

KW - Amino acids

KW - Pipecolic acid

KW - Piperidine

KW - Total synthesis

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U2 - 10.3390/molecules191219516

DO - 10.3390/molecules191219516

M3 - Article

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VL - 19

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EP - 19531

JO - Molecules

JF - Molecules

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