SYNTHESES OF (+ -)-[(CO2H)-C-14] JASMONIC ACID AND ITS PURE ENANTIOMERS/

Authors
LOREAU O BOULLAIS C NOEL JP MIOSKOWSKI C
Citation
O. Loreau et al., SYNTHESES OF (+ -)-[(CO2H)-C-14] JASMONIC ACID AND ITS PURE ENANTIOMERS/, Journal of labelled compounds & radiopharmaceuticals, 41(2), 1998, pp. 159-170
Citations number
17
Categorie Soggetti
Chemistry Analytical","Chemistry Medicinal","Biochemical Research Methods
Journal title
Journal of labelled compounds & radiopharmaceuticals → ACNP
ISSN journal
03624803
Volume
41
Issue
2
Year of publication
1998
Pages
159 - 170
Database
ISI
SICI code
0362-4803(1998)41:2<159:SO(-JA>2.0.ZU;2-Y
Abstract
(+/-)-Jasmonic acid (JA) was converted in 67% yield to the next lower bromomethyl derivative 2 by bromodecarboxylation following Barton's pr ocedure. Protection of the 3-keto group by ketalization (ethanediol), condensation with (KCN)-C-14 (DMSO) and deprotection gave the [(CN)-C- 14] nitrile 6. The diasteroisomeric semioxamazone derivatives 8a, 8b w ere resolved by flash chromatography. The hydrolysis of the nitriles 6 a, 6b successively by NaOH, then 3N HCl gave (+)-[(CO2H)-C-14] JA and (-)-[(CO2H)-C-14] JA of high enantiomeric purity (ee greater than or e qual to 98%).