Synthesis of bicyclic and tricyclic 7-oxa prostaglandin endoperoxide analogs via oxypalladation of norbornadiene

摘要

Bicyclic oxa prostaglandin endoperoxide analogs, and tricyclic oxa prostaglandin analogs are prepared by reacting norbornadiene palladium dichloride with tertiary butyl-6-hydroxyhexanoate in an oxypalladation reaction to provide an oxypalladium intermediate which can subsequently be elaborated into bicyclic and/or tricyclic 7-oxa prostaglandin endoperoxides. If the intermediate is carbonylated in the presence of an organic amine, preferably diisopropylethylamine, the compound is bicyclic; if the amine is eliminated, the compound is tricyclic. The analogs are novel compounds.