Dearomative Transformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones via Oxidopyridinium/o-Quinodimethane (5 + 4) Cycloaddition

We report the dearomative transformation of pyridin-3-ols via oxidopyridinium (5 + 4) cycloaddition with o-quinodimethanes, leading to 2,3,6,7-tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones. The chemoselective derivatization of the obtained cycloadduct was also investigated to demonstrate the synthetic potential of the obtained cycloadduct.