Natural products containing 1,4-benzodioxin have demonstrated a wide variety of biological properties such as cytotoxic and hepatoprotective effects. Despite interest in their biological activity, the synthesis of 1,4-benzodioxin has proven difficult. Previous synthetic efforts have been made to generate the benzodioxin ring structure from catechols via a catalytic free radical reaction. A method for preparing substituted 1,4-benzodioxin rings with high regioselectivity is reported. 3-Benzyloxy-1,2-o-quinone is prepared using commercially available pyrogallol, via a four-step synthesis. The o-quinone is then coupled with an enamine via an inverse electron demand hetero Diels-Alder reaction. Regioselectivity was obtained using a number of metal catalysts.

Regioselective ortho-quinone cycloaddition reactions in preparing 1,4-benzodioxin based natural products

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.