Synthesis of (2-fluorophenyl) and (4-fluorophenyl)-(2-nitromethyl)-methanones as precursors of fluorinated prostanoids

Abstract

The synthesis of new fluorinated primary nitrocompounds ?(2-fluorophenyl)and (4-fluorophenyl)-(2-nitromethylcyclopentyl)methanones has been realized by the nitromethane 1,4-addition to 1-acylcyclopentenes, available by the reductive cleavage of corresponding cyclopent-5-en[d]isoxazolines. The obtained nitrocompounds are the precursors of new fluorinated prostaglandin analogues, which could be synthesized via the formation of second prostanoids side chain by nitrile oxides method.