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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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2010.10.086
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.
| 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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