Synthesis of methyl (1R,2S)-2-[(1′Z,4′Z,7′Z)-hexadeca-1′,4′,7′-trienyl]cyclopropanecarboxylate: a potential inhibitor of the enzyme 5-lipoxygenase

Abstract

We describe the synthesis of a novel cyclopropyl analogue of arachidonic acid via a convergent synthesis that employed methyl (1R,2S)-2-formylcyclopropanecarboxylate in conjunction with the ylide from (3Z,6Z)-pentadeca-3,6-dienyl(triphenyl)phosphonium iodide. This compound was designed to inhibit the enzyme 5-lipoxygenase after reaction to form a putative α-cyclopropylmethylene radical.