Synthesis of 1-(2-Carboxyethylbenzyl)-2-benzenesulfonamidobicyclo[2.2.1]heptane: A Novel Potent Thromboxane Antagonist

A potent thromboxane antagonist, 1-[2-(2-carboxyethyl)benzyl)]-2-benzenesulfonamidobicyclo-[2.2.1]heptane was synthesized from norcamphor in 8 steps. It was shown to be a very potent thromboxane antagonist by inhibition of platelet aggregation induced by U46,619 at nanomolar concentration. The key intermediate 3-[2-bromomethylphenyl]propyl tetrahydropyran ether may be useful for the synthesis of other interphenylene containing prostaglandin analogs.