New synthetic pathways to polyfluoroalkyl containing amino- and hydroxy acids with potential biological activity

Basic data for this project

Description

This project is designed to broaden the synthetic basis for different fluorinated analogues of natural products, which are expected to exhibit biological activity. Based on the readily available 4-ethoxy-l,l,l-trifluorobut-3-en-2-one (synthetic equivalent of trifluoroacetylacetaldehyde) the stereoselective synthesis of 3-amino-6-polyfluoroaIkyl-2-pyrones and related pyridones is scheduled. These unsaturated heterocycles will be hydrogenated stereoselectively and the products will be opened to give 2-amino-5-hydroxy- or corresponding 2,5-diamino-5-polyfluoroalkylpentanoic acids, in which the latter can be seen as polyfluoroalkylated ornithines. 2-Amino-5-hydroxy-5-polyfluoroalkylpentanoic acid esters will be used to prepare hitherto unknown 5-polyfluoroalkylprolines. Moreover, 4-ethoxy-l,l,l-trifluorobut-3-en-2-one will be applied to synthesize racemic polyfluoromethylated camitine derivatives, which will be resolved by enzymatic reactions. Finally, using the same starting material, several polyfluorinated analogs of mevalolactone will be prepared.