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|Title:||A simple method for the preparation of 3-hydroxyiminodehydroquinate, a potent inhibitor of type II dehydroquinase|
|Author:||Le Sann, C.|
|Citation:||Journal of the Chemical Society. Perkin Transactions 1, 2002; 18(18):2065-2068|
|Publisher:||Royal Society of Chemistry|
|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|
|Appears in Collections:||Chemistry publications|
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