Synthesis of 5-homoshikimic acid and some fluorinated derivatives as potential inhibitors of 5-enolpyruvylshikimate-3-phosphate synthase

Article abstract of DOI:10.1016/S0040-4020(01)89449-7

The synthesis of (±)-5-homoshikimic acid, its 5-fluromethyl and difluoromethyl analogues are described from the cycloadducts of 5,6-dihydro-1-(t)butyloxycarbonylpyridine and methyl acrylate. The adducts on ring opening afford methyl 5-(t)butoxycarbonylmethyl-5,6-dihydrobenzoate, which may be 3,4-cis-dihydroxylated and converted in a series of steps into the title compounds.