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Total synthesis of natural cis-3-hydroxy-l-proline from d-glucose

✍ Scribed by Navnath B. Kalamkar; Vijay M. Kasture; Dilip D. Dhavale

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
265 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

Synthesis of cis-3-hydroxy-L-proline from D-glucose is reported. The methodology involves conversion of D-glucose into N-benzyloxycarbonyl-c-alkenyl amine which on 5-endo-trig-aminomercuration gave the pyrrolidine ring skeleton with sugar appendage in 25% yield. Alternatively, N-benzyloxycarbonyl-c-alkenyl amine on hydroboration-oxidation, mesylation and intramolecular S N 2 cyclisation afforded pyrrolidine ring compound in high yield. Hydrolysis of 1,2-acetonide functionality, NaIO 4 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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