Total synthesis of natural cis-3-hydroxy-L-proline from D-glucose

Kalamkar, Navnath B. ; Kasture, Vijay M. ; Dhavale, Dilip D. (2010) Total synthesis of natural cis-3-hydroxy-L-proline from D-glucose Tetrahedron Letters, 51 (51). pp. 6745-6747. ISSN 0040-4039

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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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Carbohydrates; Hydroxyprolines; Amino Acids; Pyrrolidine; Total Synthesis
ID Code:87228
Deposited On:16 Mar 2012 06:14
Last Modified:19 Mar 2012 11:32

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