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Syntheses of (±)‐[ 14 CO 2 H] jasmonic acid and its pure enantiomers
Author(s) -
Loreau Olivier,
Boullais Claude,
Noel JeanPierre,
Mioskowski Charles
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199802)41:2<159::aid-jlcr67>3.0.co;2-v
Subject(s) - chemistry , nitrile , enantiomer , jasmonic acid , hydrolysis , yield (engineering) , derivative (finance) , organic chemistry , acid hydrolysis , salicylic acid , biochemistry , materials science , economics , financial economics , metallurgy
(±)‐Jasmonic acid (JA) was converted in 67% yield to the next lower bromomethyl derivative 2 by bromodecarboxylation following Barton's procedure. Protection of the 3‐keto group by ketalization (ethanediol), condensation with K 14 CN (DMSO) and deprotection gave the [ 14 CN] nitrile 6 . The diasteroisomeric semioxamazone derivatives 8a , 8b were resolved by flash chromatography. The hydrolysis of the nitriles 6a , 6b successively by NaOH, then 3N HCl gave (+)‐[ 14 CO 2 H] JA and (−)‐[ 14 CO 2 H] JA of high enantiomeric purity (ee≥98%). © 1998 John Wiley & Sons, Ltd.