Total synthesis of natural cis-3-hydroxy-l-proline from d-glucose |
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Authors: | Navnath B Kalamkar |
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Institution: | Department of Chemistry, Garware Research Centre, University of Pune, Pune 411 007, India |
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Abstract: | Synthesis of cis-3-hydroxy-l-proline from d-glucose is reported. The methodology involves conversion of d-glucose into N-benzyloxycarbonyl-γ-alkenyl amine which on 5-endo-trig-aminomercuration gave the pyrrolidine ring skeleton with sugar appendage in 25% yield. Alternatively, N-benzyloxycarbonyl-γ-alkenyl amine on hydroboration-oxidation, mesylation and intramolecular SN2 cyclisation afforded pyrrolidine ring compound in high yield. Hydrolysis of 1,2-acetonide functionality, NaIO4 cleavage followed by oxidation of an aldehyde into acid and hydrogenolysis afforded cis-3-hydroxy-l-proline in overall 29% yield from d-glucose. |
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Keywords: | Carbohydrates Hydroxyprolines Amino acids Pyrrolidine Total synthesis |
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