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

Christine Le Sann, C. Abell, A.D. Abell

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

A number of routes to hydroxyiminodehydroquinate, 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 did give the desired product but in low overall yield. An alternative BBA protection strategy starting with a protected dehydroquinate was successful in generating a C4/C5 analogue of the desired oxime in high yield. Further investigation revealed that it was unecessary to protect the dehydroquinate precursor, hence the potassium salt corresponding to the desired oxime was simply synthesised as a single isomer from methyl dehydroquinate.
Original languageEnglish
Pages (from-to)2065-2068
Number of pages4
JournalJournal of the Chemical Society - Perkin Transactions 1
Volume18
Issue number18
DOIs
Publication statusPublished - 2002

ASJC Scopus subject areas

  • Chemistry(all)

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