N. Kalamkar, V. M. Kasture, D. Dhavale
Dec 22, 2010
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Influential Citations
13
Citations
Journal
Tetrahedron Letters
Abstract
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.