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Synthesis of original fluorinated cyclopropylcarboxylates

Organofluorine compounds constitute a large part of all the drugs, crop protection agents and advanced materials produced nowadays. Therefore, there is a great interest in developing the new methods of synthesis of organofluorine compounds. In this thesis we report a novel method of synthesis of monofluorinated cyclopropanes based on the Michael-initiating ring closure (MIRC) reaction. Our method allows obtaining polysubstituted monofluorinated cyclopropanes from ethyl dibromofluoroacetate and various Michael acceptors. We have also implemented the asymetric version of cyclopropanation using a novel oxazolodinone-derived chiral fluorinated reagent. In the final part of this thesis we report the synthesis of a fluorinated analog of L-FAP4, a potent agonist of group II metabotropic glutamate receptors (mGluR II). Incorporation of a fluorine atom is expected to increase the biological activity and bioavailabiblity of this compound.

Identiferoai:union.ndltd.org:CCSD/oai:tel.archives-ouvertes.fr:tel-00924650
Date22 November 2013
CreatorsIvashkin, Pavel
PublisherINSA de Rouen
Source SetsCCSD theses-EN-ligne, France
LanguageEnglish
Detected LanguageEnglish
TypePhD thesis

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