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https://hdl.handle.net/2440/37550
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Type: | Journal article |
Title: | A simple method for the preparation of 3-hydroxyiminodehydroquinate, a potent inhibitor of type II dehydroquinase |
Author: | Le Sann, C. Abell, C. Abell, A. |
Citation: | Organic and Biomolecular Chemistry, 2002; 18(18):2065-2068 |
Publisher: | Royal Society of Chemistry |
Issue Date: | 2002 |
ISSN: | 1472-7781 1364-5463 |
Statement of Responsibility: | Christine Le Sann, Chris Abell and Andrew D. Abell |
Abstract: | A number of routes to 3-hydroxyiminodehydroquinate 4, one of the most potent inhibitors of type II dehydroquinase that is currently known, have been investigated. Methods based on the existing literature synthesis, i.e. oxime formation of a suitably C-4 and C-5 protected methyl 3-dehydroquinate derivative were initially studied. Benzoyl protection as in 11 did give the desired product but in low overall yield. An alternative BBA protection strategy starting with 7 was successful in generating a C-4/C-5 analogue of the desired oxime 4 in high yield. Further investigation revealed that it was unnecessary to protect the dehydroquinate precursor, hence the potassium salt corresponding to oxime 4 was simply synthesised as a single isomer from methyl dehydroquinate 10. |
Description: | © Royal Society of Chemistry 2002 |
DOI: | 10.1039/b206066c |
Published version: | http://dx.doi.org/10.1039/b206066c |
Appears in Collections: | Aurora harvest Chemistry publications |
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