Kalamkar, Navnath B. ; Kasture, Vijay M. ; Dhavale, Dilip D. (2008) Chiron approach to the synthesis of (2S,3R)-3-hydroxypipecolic acid and (2R,3R)-3-hydroxy-2-hydroxymethylpiperidine from D-glucose Journal of Organic Chemistry, 73 (9). pp. 3619-3622. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo702749r
Related URL: http://dx.doi.org/10.1021/jo702749r
Abstract
chiron approach from d-glucose for the total synthesis of (2S,3R)-3-hydroxypipecolic acid (-)-1a and (2R,3R)-3-hydroxy-2-hydroxymethylpiperidine (-)-2a is reported. The synthetic pathway involves conversion of d-glucose into 3-azidopentodialdose (5) followed by the Wittig olefination and reduction to give the piperidine ring skeleton (8) with a sugar appendage that on cleavage of an anomeric carbon followed by oxidation gives (-)-1a which on reduction affords (-)-2a.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 75333 |
| Deposited On: | 22 Dec 2011 13:12 |
| Last Modified: | 22 Dec 2011 13:12 |
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