Applications of (4+3) cycloaddition reactions of furfuryl cations

A novel Lewis acid-promoted (4+3) cycloaddition between a furfuryl alcohol and a diene was recently developed in our lab and was schown to be a quite general and straightforward synthetic process for furan-fused seven mebered rings (2-oxa-hydroazulenes). In this poster presentation, we report the rapid synthesis (1-3 steps) of various polycyclic scaffolds, incorporating a fused cycloheptene and furan ring, starting from cheap and simple furan diene substrates, derived from natural sources. The results presented herein, further validate the newly developed cycloaddtion process as a syntheic method. Furthermore, preliminary results will be discudded from a study in which various oxidative conversions of these polycyclic scaffolds are performed in order to generate natural products like libraries with pontentially intresting biological profiles.

Publication year:2012