Jump to main content
Jump to site search

Issue 18, 2002
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Publication details

The article was received on 24 Jun 2002, accepted on 24 Jul 2002 and first published on 16 Aug 2002


Article type: Paper
DOI: 10.1039/B206066C
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 2065-2068
  •   Request permissions

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

    C. L. Sann, C. Abell and A. D. Abell, J. Chem. Soc., Perkin Trans. 1, 2002, 0, 2065
    DOI: 10.1039/B206066C

Search articles by author

Spotlight

Advertisements