Synthesis of Fluorine Analogues of Vitamin E

As part of a search for biologically active analogues of vitamin E, fluorine derivatives of tocotrienol and related compounds were synthesized by the ring-closure of trifluoroprenols with trimethylhydroquinone. For this purpose, the trifluoroprenols were synthesized by the Wittitg-Horner reaction of trifluoroacetone or its prenyl homologues with triethylphosphonoacetate followed by reduction of the trifluoromethylated acrylic ester derivatives. Although 4, 4, 4-trifluoroprenol itself did not react with the hydroquinone, 7, 7, 7-trifluorodiprenol and higher prenols gave 6-chromanols with a trifluofomethylated side-chan.