Synthesis of prostanoids with bicyclo[2.2.1]heptane, bicyclo[3.1.1]heptane, and bicyclo[2.2.2]octane bicycloAD2.2.2BDoctane ring systems. Activities of 15-hydroxy epimers on human platelets

Article abstract of DOI:10.1021/jm00347a004

A number of prostanoids with bicyclo[2.2.1]heptane, bicyclo[3.1.1]heptane, and bicyclo[2.2.2]octane ring systems have been prepared by routes which allow the introduction of the ω chain after the α chain. The introduction of a 16-p-halophenoxy substituent confers platelet aggregation activity on both 15α- and 15β-hydroxy epimers. In the case of the pinane thromboxane ring system, the natural ω-chain compound is an inhibitor of aggregation, whereas the 16-p-fluorophenoxy analogue is a potent aggregation agent.