Reference : NUCLEOPHILIC ENANTIOSELECTIVE SYNTHESIS OF 6-[F-18]FLUORO-L-DOPA VIA 2 CHIRAL AUXILIARIES
Scientific journals : Article
Physical, chemical, mathematical & earth Sciences : Chemistry
Human health sciences : Radiology, nuclear medicine & imaging
http://hdl.handle.net/2268/5454
NUCLEOPHILIC ENANTIOSELECTIVE SYNTHESIS OF 6-[F-18]FLUORO-L-DOPA VIA 2 CHIRAL AUXILIARIES
English
Lemaire, Christian mailto [Université de Liège - ULg > > Centre de recherches du cyclotron >]
Plenevaux, Alain mailto [Université de Liège - ULg > > Centre de recherches du cyclotron >]
Cantineau, Robert [> > > >]
Christiaens, Léon [> > > >]
Guillaume, Marcel [> > > >]
Comar, Dominique [> > > >]
1993
Applied Radiation & Isotopes
Pergamon Press
44
4
737-744
Yes (verified by ORBi)
International
0969-8043
Oxford
United Kingdom
[en] Asymmetric nucleophilic synthesis of 6-[F-18]fluoro-L-dopa was investigated in order to reach an enantiomeric excess of close to 100% of the L form of this amino acid. The radiochemical synthesis required [F-18]fluoride as fluorinating agent and regioselective nucleophilic substitution of commercially available 6-nitroveratraldehyde. The [F-18]fluorobenzaldehyde thus obtained was easily converted to the corresponding 2-[F-18]fluoro-4,5-dimethoxybenzyl bromide. This alkylating agent was added to the lithium enolates of 1-(S)-(-)camphor imine of t-butyl glycinate (1) and (S)-(-)- 1 -Boc-2-t-butyl-3-methyl-4-imidazolidinone [(S)- Boc-BMI] (2) in order to compare the enantiomeric excess of the L form obtained in each case with these two chiral inductors. The L-isomer of fluorodopa was isolated after H1 hydrolysis and HPLC purification in 5-10% radiochemical yield (decay corrected). The overall synthesis time was of 110 min. Through this synthetic pathway, the L-isomer of fluorodopa was obtained in 83% e.e with 1 and 96% e.e with 2 respectively, as determined by chiral HPLC. A practical three step preparative scale synthesis of 6-[F-19]fluoro-D,L-dopa is also presented.
Centre de Recherches du Cyclotron - CRC
Fonds de la Recherche Scientifique (Communauté française de Belgique) - F.R.S.-FNRS
Researchers ; Professionals ; Students
http://hdl.handle.net/2268/5454

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