An efficient approach to d-threo-3-hydroxyaspartic acid for the synthesis of novel l-threo-oxazolines as selective blockers of glutamate reversed uptake |
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Authors: | Meri De Angelis |
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Institution: | Dipartimento Farmaco Chimico Tecnologico, via Aldo Moro and European Research Centre for Drug Discovery and Development, Siena University, 53100 Siena, Italy |
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Abstract: | An efficient, stereoselective synthetic strategy to d-threo-3-hydroxyaspartic acid was developed. Starting from l-(2S,3S)-N-benzoyl-3-hydroxyaspartic acid dimethyl ester by a Deoxo-fluor-catalyzed cyclization reaction, an inversion of configuration at the β-center (erythro isomer), was observed. A base-induced epimerization reaction led to the d-trans-isomer, which was hydrolyzed to give d-threo-3-hydroxyaspartic acid with excellent stereoselectivity and overall yield. Starting from d-threo-3-hydroxyaspartic acid, l-threo-oxazolines can be stereoselectively synthesized. |
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Keywords: | d-threo-3-Hydroxyaspartic acid" target="_blank">d-threo-3-Hydroxyaspartic acid Glutamate l-threo-Oxazolines" target="_blank">l-threo-Oxazolines l-t-3OHAsp" target="_blank">l-t-3OHAsp |
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