Kondratov I. Fluorinated analogs of mevalonic and mevaldic acids

Synthesis of fluorinated analogs of natural compounds from accessible fluoroorganic sintons. Receipt of enantiomeric clean fluorinated analogs of mevalonic acid and establishment of their absolute configuration, and also synthesis of fluorinated analogs of mevaldic acid from derivative fluorinated b-ketoaldegids as initial compounds. Chemical synthesis, IR- and РMR-spectroscopy, chromatography. Synthesis of racemic mevalonic and mevaldic acid fluoroanalogs and enantiomerically pure mevalonic acid fluoroanalogs starting from fluorinated ?-ketoaldehyde derivatives. At the time of investigation the new fluorinated ?-ketoaldehyde derivatives (including chiral derivatives) were synthesized. Such nucleophilic reactions: reduction, Wittig, Reformatsky, aldol reaction with obtained fluorinated ?-ketoaldehyde derivatives were studied. Aldol reaction with ?-ketoaldehyde derivatives was used for synthesis of racemic 6,6-difluoromevalonate, 6,6,6-trifluoromevalonate, 6,6-difluoromevaldate, 6,6,6-trifluoromevaldate. Obtained racemic fluoromevalonates were separated on enantiomers. Both enantiomers of 6,6,6-trifluoromevalonate were tested as immunomodulators and significant differences were found between their bioactivities. The new polyfluoralkyl dehydropyrones and pyrones were synthesized. Sphere of use - bioorganic and organic chemistry.