A simple method for the preparation of 3-hydroxyiminodehydroquinate, a potent inhibitor of type II dehydroquinase

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dc.contributor.authorLe Sann, C.
dc.contributor.authorAbell, C.
dc.contributor.authorAbell, A.
dc.date.issued2002
dc.description© Royal Society of Chemistry 2002
dc.description.abstractA 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.
dc.description.statementofresponsibilityChristine Le Sann, Chris Abell and Andrew D. Abell
dc.identifier.citationOrganic and Biomolecular Chemistry, 2002; 18(18):2065-2068
dc.identifier.doi10.1039/b206066c
dc.identifier.issn1472-7781
dc.identifier.issn1364-5463
dc.identifier.orcidAbell, A. [0000-0002-0604-2629]
dc.identifier.urihttp://hdl.handle.net/2440/37550
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.source.urihttps://doi.org/10.1039/b206066c
dc.titleA simple method for the preparation of 3-hydroxyiminodehydroquinate, a potent inhibitor of type II dehydroquinase
dc.typeJournal article
pubs.publication-statusPublished

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